


Cheating Derek: The One About the Prom

by Always_Bottom_Derek, IcyCryos



Series: Cheating Derek Series [2]
Category: Buffy the Vampire Slayer, Teen Wolf (TV)
Genre: A Couple Other Crossover References Besides Buffy, Anal Sex, Bi Stiles, Bottom Derek Hale, Bullying, Cheating, Come Swallowing, Dildos, Dubious Consent, Gangbang, If You Ship Sterek You Will Not Like This. So Please Don't Read It And Then Yell at Me About It, M/M, No Way Around It, Oral Sex, Pegging, Polyamorous Stiles, Revenge, Sex Addict Derek Hale, Slight Femdom, Spitroasting, relationship dissolution, this is just pure filth
Language: English
Status: In-Progress
Published: 2017-06-19
Updated: 2017-09-05
Packaged: 2018-11-15 23:54:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 21,105
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11241915
Author URL: https://archiveofourown.org/users/Always_Bottom_Derek/pseuds/Always_Bottom_Derek, https://archiveofourown.org/users/IcyCryos/pseuds/IcyCryos
Summary: I love cheating Derek fics.Love, love, love them.With an overt cheating fic, it's really the thrill and the disregard for the sanctity of relationship. And a cheating story is infinitely better when the cheated-on partner finds out. And personally, I really like it when it's a situation where the one that is cheating gives more to the cheating relationship than to the actual relationship. Which is why I LOVE when Derek bottoms with the guys outside his relationship and tops with Stiles: Stiles doesn't even get that part of him, but the anon(s) do(es).Say for example… Stiles is 100% invested in this relationship. Giving it his all. While Derek is slutting it up with the whole sheriff’s department. All the deputies making inside jokes when Stiles visits. Poor Stiles, completely oblivious when Derek excuses himself during one of their office calls and leaves him talking to his dad while his boyfriend goes to the bathroom to let Jordan use him...





	1. Cheating Derek I: The One About the Prom

**Author's Note:**

> This is first in a series of what was supposed to be drabbles. But I am a wordy fucker. Clearly.
> 
> So, these stories follow the same theme as the rest of my works here: Derek gets used. That's about it, although I try to be at least a little artful about it. And these stories are not just mine, but are essentially a dolling up of chats I've had with writer IcyCryos about how to fictionally (key word here) use and abuse Derek.
> 
> Anyway, I proposed sharing these with a larger readership and my cyber pal wasn't opposed. So here's the first. Hope it entertains.

_I love cheating Derek fics._

_Love, love, love them._

_With an overt cheating fic, it's really the thrill and the disregard for the sanctity of relationship. And a cheating story is infinitely better when the cheated-on partner finds out. And personally, I really like it when it's a situation where the one that is cheating gives more to the cheating relationship than to the actual relationship. Which is why I LOVE when Derek bottoms with the guys outside his relationship and tops with Stiles: Stiles doesn't even get that part of him, but the anon(s) do(es)._

Say, for example… Stiles is 100% invested in this relationship. Giving it his all. While Derek is slutting it up with the whole sheriff’s department. All the deputies making inside jokes when Stiles visits. Poor Stiles, completely oblivious when his boyfriend excuses himself during one of their office calls and leaves him talking to his dad while Derek goes to the bathroom to give Jordan a blowjob or a quickie.

Of course, you know to make it perfect, John would be in on it too. Hating himself but unable to resist bending Derek over and plowing his son's boyfriend's lush ass at every opportunity. He’s conflicted of course, he's got a heart after all. He wants Stiles to be happy and Derek makes Stiles incredibly so. And maybe, John reasons, if he and his deputies fuck Derek enough, it will keep his son’s slutty beau from going out and getting his needs met elsewhere.

_Better to keep it in the family, so to speak. Right?_

Meanwhile, naive Stiles thinks it's great that Derek wants to hang out with his dad. After all, Derek doesn’t have a father of his own anymore and probably misses that relationship. And Derek’s considerably older than he is, closer to the age of the deputies, so a little bro time with contemporaries is to be understood. I mean, Derek never takes issue when Stiles spends some much needed time with Scott.

So, yeah. Stiles doesn’t mind sharing Derek with the sheriff, or the rest of his crew. In fact he wholeheartedly supports his individual trips down to the station because Derek always seems so relaxed and so much more content afterwards.

_Little does he know his beloved boyfriend’s really just going over to be bred._

So, while Stiles is happy they’re all getting along and his normally loner guy has found some peeps, the Sheriff and his deputies are enjoying the hell out of rough fucking, nipping, and spanking Derek, knowing any bruises will go away by the time their fucktoy gets back to Stiles.

And since he doesn’t have special werewolf hearing, or that great sense of smell, maybe Stiles has even come into the station to see his dad once or twice while Derek is under the desk warming the sheriff's cock.

_Mmmm. Yes._

You have to admit part of the thrill in cheating is the possibility of being caught, and Derek’s no different in that regard. He really doesn’t want to devastate Stiles but the potential humiliation of being caught with his lips wrapped around such an oh so suckable cock makes his own leak like Niagra. Not to mention after a close call like that, John, reacting from his own shame at the situation, is always so much harder on him. Punishes him wonderfully.

Yep, the sheriff would like to end things, he really would. But he and his guys have become addicted to pounding that delicious round, firm ass. They love the way his werewolf powers make Derek’s hungry cunt snap back to virginal tightness, no matter what they stick up there. And the things Derek can do with his mouth… Holy fuck.

So, there’s no way in hell John can bring himself to end this. In fact as things go along, there’s days he feels selfish and doesn’t want to share Derek. When that mood strikes him, he drives just the two of them out into the boonies in his squad car and fucks his bitch against the hood, catching all the action on his cruiser cam so he has something to jerk off to later once he releases Derek to go back to his son.

In retaliation for John hogging their favorite fuckwolf and doing the dirty outside the station, inevitably all the deputies try to outdo themselves and hold a contest where they vie for who can fuck Derek in the most outrageous place.

John still wins, of course. There’s a reason he’s the sheriff. He uses his cunning and Derek’s man cunt and, once he finds out about their little contest, he beats them all by fucking their sweet werewolf bitch in Stiles' boyhood bed.

And as much as they hate to admit it, the deputies have to agree that the balls of this even beats the night they handcuffed Derek naked in the drunk tank. Cuffs locked to the bars after a rowdy bunch of inebriated bikers were brought in for a roadhouse brawl. Although everyone at the station acknowledged watching those beer bellies bounce off Derek’s tight ass, him struggling to swallow those rank cocks, his nose pressed deep into multiple untamed thatches of sweaty, pissy pubic hair… That was be a treat indeed.

_Oh, yes.  
_

And after Derek was well and thoroughly fucked that night, just maybe the boys cuffed him to the cell's single toilet so that Derek could enjoy the full experience of all the sated bikers’ whiskey and beer and drunken aim.

_Now that night would be a hell of a story, but  I’m afraid I’m digressing._

_So, back to the topic of cheating fics._

The best part of a good cheating fic is the reveal. _Terrible, but true._ That moment when the cuckolded lover discovers the truth and the emotional chaos ensues. So now that I’ve set up as much of a premise as one needs for passable porn, we’re brought to how would this particular story end?

How does Stiles find out his gorgeous boyfriend, the Adonis he pined after and finally bagged, the stoic sourwolf he shares so many tiny tender moments with when it’s just them, how does he find out that not only has his beloved been cheating (with his FATHER), but that Derek’s actually the personal cunt for the whole Sheriff’s department?

_Well. In best/worst case scenario it should be dramatic and demeaning._

Let’s say for shits and giggles, for this story, because there are few moments more significant and dramatic nights in a teenager's life, that the occasion for the cheating reveal here is prom night.

_Yes, prom night will do nicely._

Dear blissfully ignorant Stiles plans his perfect prom. Of course, Derek can't actually go to the dance with him because he’s like twenty-six to Stiles’ eighteen and that would just look creepy. Even if Stiles is finally legal now. But still, Derek agrees to go along otherwise with the whole shebang. Because even though he is a compulsive whore who can’t get enough law enforcement dick in his holes, he really does love his boyfriend and Stiles is kind of adorable in his spastic excitement about the event.

Keeping the peace, the sheriff is there at the Stilinski home like a good daddy should be on that fateful night when Derek shows, dressed to the nines to pick his clueless kid up. John has to excuse himself to call Stiles down and steal a few seconds to tuck his erection up behind his belt at the sight of the station's slut looking so gorgeous. Derek’s not in tux… he couldn’t bring himself to be so corny, not even for Stiles, but he still looks like a god in the sleek suit he’s wearing, one that must have cost at least a couple months of law enforcement wages.

Seeing Derek like this, John want’s to strip Derek to the bone and fuck him broken.

But instead, he takes their prom pictures at the house. Stiles looking actually quite sharp in the tux he insisted on wearing, though clearly Derek had a hand in picking it out. Yeah, John’s boy is so happy, grinning like a goof and giddy almost to the point of giggles next to his sober lover.

The sheriff snaps over a dozen pictures on Stiles' and Derek's’ phones and his own old fashioned camera, all the while hoping that the precome leaking from his dick doesn’t wick through the fabric of the khakis he’s still wearing enough to become visible. But how can his cock not weep though when throughout the young couple’s poses, all he can think about about is the file of pornographic shots he has of his son’s boyfriend on his laptop? The pictures in his own private stash he’s going to pull up and yank to as soon as his son and his date are out of sight.

Pics from his and his deputies' phones showing Derek, spread-eagled all over the station, dick hard and dripping. Bent over, grabbing and spreading his cheeks, revealing that bottomless ass pussy of his. Derek with deputy cock in both of his ends, spit-roasted and drooling spunk from every loaded hole. And, of course, the ever orgasm inducing photo shoot he did of Derek the time he fucked him in Stiles' bed. Derek tangled up in in his son’s Star Wars sheets, covered in cum and looking completely fucked out, both holes red and momentarily swollen from use.

_Again… Digressing. Can’t help it. Imagining Derek in all these ways… It just gets my motor revving._

But putting the brakes on. Again. Back to our original track: Derek escorts Stiles to the dance venue. Rather than his normally too cool for school car, he goes the extra mile and rents a limo. Drops Stiles off with a hot as hell kiss the kid can feel all the way from the tips of his buzz cut to his newly trimmed toenails. He whispers sweet dirty words and filthy promises in that rough voice of his into his younger lover’s ears between none too gentle nips.

Tells Stiles he’s taking the limo to the penthouse suite he’s rented at Beacon Hills’ nicest hotel and he’ll send the car back later. No worries about the time, he’s booked the car for the entire night. Although, *wink* of course, the sooner Stiles returns to him, the sooner they can get down to making good on all those explicit whispers.

_Cause everyone knows the prom itself is only a small part of the equation. It’s what happens after that really is the sum of the whole event._

High on kisses and his astoundingly good luck to have miraculously nabbed such a great boyfriend, Stiles all but floats into the dance. Wanting to share his good fortune and convinced he’s about to have the night of his life, his big mouth tells anyone who’ll listen, just short of the entire prom, about how his smoking hot, older boyfriend rented a room for them and how he is going to have THE BEST after prom after-party in the history of Beacon Hills proms.

_Yeah, this setup is golden. Now how does the big reveal occur?_

Maybe, near the end of the night, there is a commotion by the entrance of the venue. Word spreads and the entire school goes outside to see what it's about.

And....

Stiles steps outside and what does he see?

Flashing police lights. And his boyfriend. Spread out in the hood of the limo. Getting spit roasted by two deputies and jacking off a third. Completely naked. The deputies in full uniform. Only their dicks out.

Slut Derek never made it out of the parking lot. You see, though normally so stoic, slutty-wolf can have a big mouth too ( _not just in the instance of gobbling cock_ ). He couldn’t help but brag of his plans for Stiles’ prom to the deputies the last time he was gangbanged. Maybe even mentioned this was the first time. THE FIRST! He was going to bottom for Stiles.

Helpful bunch that they are, the deputies pulled the limo over on the way out of the lot to get their favorite fuckmeat prepped for the big event. Even though they knew if they fucked him too early he’d be vice tight again before Stiles got to him. Of course, despite his initial protests, once Derek got that first whiff of deputy dick his addiction for fat, lawful cock kicked in and he couldn’t get enough. And the guys got so turned on they forgot to shut off their lights.

Derek’s suit had the same effect on them it did John, only they weren’t under the same constraints as the sheriff.

Chalk that up as a win for the underlings.

But, poor Stiles.

_Or… If that scenario seems to far fetched (Ah, who am I kidding? They’re all farfetched, this is fucking porn after all) let’s try on another possibility._

Maybe Derek does make it off the lot, but the guys pull him over  this time on the way to the hotel. Book him on a bogus charge. Haul that fine muscular ass of his into the station. He protests and, of course, being a werewolf, if he really wanted to resist he could, no problem. But the thought of the meat waiting for him trapped behind those crisp uniforms… Well, he just can’t help himself.

Now, the deputies like Stiles and they don’t want to cause problems for the Sheriff, cause he’ll make their lives hell. But their boss has been hogging their fuckpig (p _un intended_ ) and Stiles clearly isn’t enough of a man yet to keep his sex addicted lover in line. Not to mention he will be leaving BH after graduation for college and Derek’s been making noises about following his boyfriend there. The idea of losing their bitch and going back to the humdrum of wives and girlfriends/husbands and boyfriends or lonely solo wanking is too much for them. They can’t let Derek leave, so they have to force a break up.

So then, knowing Derek and Stiles’ plans, they got into the dance before it started on a “routine check.” With all the psycho kids in the country right now, not too mention all the weird shit that happens already in their beloved Hills no one even bats an eye at this.

The deputies mess with the tech for the event so that, in the middle of the prom crowning, the projector screen on stage flickers to life and a live feed of the station pops into focus. It's Derek getting ganged by a new group in the drunk tank. Maybe this time the bangers even include some of Stiles’ classmates picked up before the prom having gotten into the juice before the event and nabbed for unruly conduct and under-aged drinking.

The video starts just when one guy is cumming in Derk. He slaps the werewolf’s already rosy ass as he pulls out and another prisoner climbs on. And meanwhile, there, in the middle of the dance floor, stands poor, crushed Stiles. All his proud words biting him in the ass while his boyfriend in monumental form, projected, is getting his ass pounded viciously now by…

_Let’s be super cruel here and say Jackson was one of the guys they picked up early. Yeah. Jackson will do nicely._

So Jackson is going to town on Derek's ass. Meanwhile, outside the cage and off camera the deputies watch masturbating. They cut the feed as soon as they're close to cumming to take advantage of Derek pressed up against the bars, mouth pussy open and hungry for them, even as his ass pussy is pummeled.

_Fuck. That's hot. Terrible. But still hot._

_Or how about this alternative. (Last one)..._

Again Stiles has bragged about how he and Derek are going to do the deed that night. This time to his friends even before the night of the dance. Like before, it's the first time Derek's going to give his ass to him.

_And now that I’ve mentioned Jackson, let’s bring him back in this scenario._

Stiles brags and Jackson catches it and flips him shit. Says he still really doesn’t even believe that Derek is Stiles’ boyfriend.

Youth and pride are not always the best partners in decision making: Stiles gets the hotel staff to let him into their suite before check in that day. He’s there just long enough to hide a few cams in the hotel room Derek reserved to prove it.

_Ooooo… Yep… You know this isn’t going to end well._

So, Derek takes the limo to the suite after dropping Stiles off to wait for him. He’s gone the whole nine yards here. Champagne and energy drinks on ice, strawberries dipped in chocolate and Stiles’ favorite junky snacks in the mini-fridge. There’s rose petals on the bed, lube and body oil on the nightstand, a sweet spicy bubble bath set on the edge of the giant, sunken tub in the room. Derek’s even got a playlist on the ready on his phone for when they’re making love. Movies queued up for the times they’re recuperating.

He wants everything to be perfect because whore or not, he's fond of the kid, you know.

Maybe he even gives himself an enema and pops in a plug so when Stiles shows up they can get right to the lovefest.

But even while he’s doing all this he can’t stop thinking about how great the Sheriff looked at his house that night. All cool and composed, though Derek could smell the man’s arousal pouring off him. And the enema just gets his ass wanting, and the plug he puts in doesn’t seem anywhere near big enough. Certainly not in comparison to what he's used to.

And the more he thinks about how sweet Stiles will undoubtedly be with him, and the fact that, for such a skinny twink, the kid does have a sizeable cock ( _good genetics, takes after his father_ ), Derek’s mouth and his ass start itching for the rough fucks of his precinct pals. The way they stuff him so good in all his hungry holes. The sweet perfume of all their mingled spunk and piss and spit and yes, sometimes shit, when they use him.

And then like an answer to his depraved prayers the sheriff shows up at the door looking like his sexual savior. Only he’s disappointed to learn John is there on business because something's going down at that same hotel and knowing Derek and his son were going to be there he wanted to warn them.

Only it’s really not all that dire. The perp is a low level scumbag. A cyber thief who’s rented a room while he hacks into the accounts of guests using the hotel’s wireless. John’s guys even know the room, thanks to the ever helpful desk staff.  And seeing Derek all alone, knowing that it will be some time until his son shows up…

Well, Derek isn’t the only one who’s been Jonesing. Jacking off to those pictures did nothing for John once the boys left the house: images just can’t compare to flesh. Particularly when that flesh is Derek’s.

Yeah, the deputies can handle the thief. In the meantime John will handle…

_Well, you get the picture._

And while Derek enjoys pounding Stiles' tight ass, he just can't resist John's thick, long man cock in his own.

_Yummmm._

Between punishing kisses and John slapping him about a bit for warm up, they agree that this will just be a quickie. The sheriff will fuck Derek on the floor so they don’t mess up the room and Derek’s rug burns will heal soon enough.

_Wham bam thank you ma'am. Or sir, in this case._

That’s how it was supposed to be anyway. But while John’s stripping Derek out of his suit and pulling the plug out of him none too kindly, his deputies catch their alleged criminal. Not too difficult: the hacker is a big guy, like say around 350 maybe 400 pounds, so he’s not the quickest on his feet.

Rather than go stick the guy in the car... Not like he'd fit easily...  Jordan knows the room number John was off to, so they head off to find their leader, hacker in tow. It's quite the little parade they make. They use the universal pass key the lady at the front desk loaned them and open the door to find the sheriff balls deep in in their bare ass naked bitch.

Now, this… Fucking Derek in the room where he’s giving his supposed ass cherry to his teenage boyfriend on his prom night… This beats the shit out of even fucking him in Stiles’ bed. And there’s no way seeing this that the guys are going to let the sheriff claim the glory of this solo. So John’s quickie quickly becomes a much longer “come one, come all” fuckfest.

The guys handcuff the fat hacker to the mini fridge to hold him while they join in. He gets excited watching all these hot, buff law men fucking the hell out of one hot, buff werewolf and starts playing with himself under all his fat rolls.

Hopped up on adrenaline from a successful bust, even if it didn’t turn out to be all that dangerous, the squad meanwhile, is being is brutal with Derek. And he loves it! It’s spit-roast, train fuck time. And in a matter of moments he’s got a cock in each hole and one in each hand. The whole room is full of moans, growls, and grunts.

One of the guys currently relegated to getting a hand job looks over and notices their criminal playing with himself. He tells him to “knock it off,” but then Jordan, has a better idea. They pull out of Derek and leave him drooling from both ends, his holes already and puffed from their poundings, while they uncuff the hacker, strip him, and stick him on the bed, crushing the rose petals.

Derek’s whimpering the whole time, so unhappy with being empty. There’s an easy remedy to shut their bitch up though. They make the hacker lay back and bury Derek’s sweaty head under his paunch, shoving Derek's mouth on the guy's cock to "shush" him while they squabble over who gets to fuck him next.

The argument leads to a male catfight of sorts, the guys, still fully dressed in their uniforms, dicks out though, hard and waggling as they shove each other around. Whoever wins is so amped up he literally slams into Derek hard enough it actually knocks the wind out of the fat guy too.

And I don’t mean just his lungs. He lets loose with a wet juicy fart of convenience store hotdogs and microwave burritos. All loose from the nerves of being caught, some shit leaks out along with his wind. It stains the white coverlet of Stiles’ bridal bed. Shit clings to the fat dude's sweaty ass along with the rose petals Derek sprinkled about earlier.

The smell of this is enough to make the guys choke and curse, but Derek just breathes it in. Too busy licking the dick cheese from the remaining wrinkles in the hacker’s foreskin. The guy’s so unhealthy even his pre tastes foul but Derek laps this up like it’s the nectar of the gods.

John opens a window, turns on the air and tells his underlings to get it in gear. They have to finish wrecking Derek so he has enough time to recover for Stiles. Not like they need any encouragement. One after the other they thrust their heavy meat into the wet mouth of Derek’s ass. They spank his plump cheeks rosy as they ride.

_Mmmm. Hot._

_So while all this is happening, did you forget Stiles had those cams in the room? Cause I can tell you someone who didn’t._

Jackson.

See, he’s heard rumors about Derek because he takes a fair amount of dick himself. Not that he broadcasts the fact. Maybe he was even the guy who tipped the Sheriff’s department about the hacker at the hotel, a nemesis of Danny's, since Stiles was motor mouth enough to tell him not just the name of the hotel in his bragging, but the particular suite too.

Whether Jackson was the tipper isn’t important. What is, however, is that he’s definitely the guy who paid Danny to hack into the feed Stiles had going from the cams to his phone. Danny’s been keeping tabs on Derek ever since he showed up to the hotel and gets so entertained (and aroused) watching the goings on, he almost forgets to let Jackson know what was going down.

_Almost._

Once Jackson gets a look at the antics occurring in Derek and Stiles’ suite, he’s raring to go. He butts into the bro dance Stiles and Scott are sharing and starts up his same rant about how Stiles was blowing smoke up his ass about his "wonderful, hot, and _devoted_ boyfriend."

And doesn’t that just piss the hell out of Stiles! Because, you see, he was checking the feed himself earlier. Saw Derek enter their room and all the sweet and wonderful things his beau was doing for him. He only stopped checking in after seeing all the trouble Derek was going to for him. It made him feel guilty for spying on him at all. Even if it was for the good cause of shutting asshole Jackson up.

Stiles says as much, and pulls out his phone. He starts tapping into the feed, fully expecting to see Derek, barefoot in his dress shirt and boxers lounging on their future bed of bliss, reading one of those dry books he favors or watching some nature program on the room’s big screen.

Before he gets his feed up already, Jackson’s given the nod to Danny.

_Here we revert back to the projection idea from earlier._

In a blast of light and sound the cam footage illuminates the prom stage, and what it shows is so far from Stiles’ imaginings.

Derek has the sheriff in his ass. _Again_. A deputy in each hand and his head still buried under belly rolls between the fat guy's thighs. Only now, Derek is on his back. Legs on the sheriff's shoulders. His head and upper body buried with the fat guy sitting on his face. His hands are busy with sticky deputy cock and his tongue is going like gangbusters on the hacker’s shitty asshole.

_Yeah.  It’s perfect._

Perfect for Jackson, who just stands there smirking like the prick he is as Stiles stares, pale, then flushed bright red; his mouth gaping open like a carp, but with no words emerging, at the video of his hot slut of a boyfriend being banged.

_Ooooo. Jackson would so do that._

Danny too, since, despite their gap on the scale of hottness, he secretly was going to gift Stiles with the honor of fucking him before Stiles so rudely got entangled with Derek.

Once the projection is on the whole prom comes to a halt. Chaperones are screeching for someone to cut the power. Poor Stiles is there surrounded by whispers and uncomfortable laughter. He does the only thing he can think of and bolts, pushing his way through stunned teenagers while Jackson cackles triumphantly behind him.

Outside he jumps into the waiting limo and bribes the guy to speed through town to the hotel. Not like there’s much traffic at that time of night. All the while he’s still watching on his phone as his dad shoots a heavy load of seed into Derek’s ass. Followed by each one of his deputies.

Stiles jumps out of the limo before it even comes to a stop. He races up to the room.

The deputies didn’t think to close it tight behind them once they saw what was going on, too eager to join in. Finding it slightly ajar, Stiles bursts in just in time to see multiple deputies cumming almost simultaneously. They spray spunk all over Derek's crotch and his belly. It drenches his huge dick, rock-hard and leaking so much he’d already made his own puddle.

Stiles yells, his dad shouts back at him. Derek, however, is all but deaf and blind to all the commotion because he's buried under all that flesh.

Now Stiles is sick with what he’s seen, but he’s also hard as a his AP physics homework, Derek’s bulging muscles have always had that effect on him. And now is no different, even though he’s thoroughly hating himself for it.  A part of him knows too that who he should really be hating, besides Jackson, is Derek.

_Yep, Stiles is heartbroken, crushed, devastated, but what’s more, he’s pissed as shit._

He pushes his father aside, cock hard as ever still, like it's been since he left the prom. Tonight was his night to fuck Derek, and as much as he hates him right now, he’s determined to go through with it. Slipping into Derek's wide open ass, slick with cum, he almost retches though at the squelching sound their joining makes when he enter Derek’s sloppy hole.

Derek is still oblivious to the owner of the new cock inside him. Even if his sensitive werewolf ears weren’t wearing earmuffs of ass fat, hearing anything over the sounds of pleasure the hacker is making would be a challenge. The guy is not caring one whit about the newcomer or the commotion. He also doesn't give a damn about who’s fucking the guy whose tongue is in his ass. He’s too busy experiencing the heaven that is an expert ass licker.

Never has he had anyone attended to his roid ridden pucker sooooo well.

Meanwhile Stiles cries as he pounds into Derek (who's still oblivious, by the way). It’s messy, his crying. Loud and broken. While his dad and the deputies watch in uncomfortable silence, his tears fall freely, adding to the other fluids painting his once beloved boyfriend’s cum-stained belly. But not all of these tears are from sorrow: Stiles is as furious as he is shattered and he rams Derek so wicked hard in his anger and betrayal.

Yeah, so maybe his cock's not quite as big as John's but he's got the power of his rage behind it.

And Derek meanwhile thinks it’s the best fuck he's had all night. Writhing and moaning while he eats fat guy out. And the hacker is close to blowing his second load. Usually one is all he can manage a night, but Derek can pull refractory in the same way he does pain. That’s just one of the reasons his tops love him so much: he makes them fucking energizer bunnies.

Anyway, the hacker is about to come just from Derek tongue fucking his now spotless asshole and so he clamors up, raising himself on his chubby knees, spreads his thighs wider. He wants his dick in that gorgeous mouth again, to come down Derek’s throat and watch that Greek god neck tense and flex as he swallows the load down.

In his repositioning he lifts off Derek enough Derek can raise his head up for the first time in ages and take a breath of air not humid with skank.

_And when he does… Well, of course he sees who it is fucking him._

Derek’s face is flushed from arousal and lack of air. He’s got traces of shit and sperm on his spit-shiny cheeks and his mouth is raw and red from use. His eyes grow huge as they lock with Stiles.

A thousand words pass unspoken between them as they hold each other’s gaze.

_Fuck… It's intense.  
_

Derek knows it’s over in an instant. That he’s crushed Stiles completely. That the best cock he’s had all night is the truest definition of a hate fuck one could find.

He knows it and he’s sorry. So sorry. It wasn’t supposed to happen like this. But who was he kidding if he said he didn’t think a moment like this wasn’t going to come at some point?

And the worst part about it is that as much as he hates what he’s done to Stiles, hates himself for wrecking the one truly good and pure thing he had going on in his life, he just can’t make himself stop. He’s a whore and he knows it. Only really happy when he’s being used and abused. And let’s face it, past this moment Stiles isn’t the kind of guy who would be able to do that.

No, if this hadn’t happened, Stiles would be the guy to cuddle and nurture him. Treat him so nicely Derek knows after a while he wouldn’t be able to stand it. So, he decides right then and there it’s best for both of them if he stops the charade, although it does make his heart ache harder than his cock ever has.

Derek breaks their eye contact first. He lays his head back down, wraps those powerful arms of his around the thief’s thunderous thighs and sucks his purpled cock into his mouth. Seeing this, Stiles is stunned stupid for the second time that night. He gawks at Derek going back to sucking fatty’s cock like it’s his job.

_Meanwhile, his teenage body is on auto pilot, still pounding away.  
_

It’s the cherry on the shit sundae of his night when Stiles, and the guy his new ex is sucking, and his new ex, come at the same time. The fat man shoots down Derek's throat. Derek’s Adam’s apple bobs as he swallows while he unloads himself, spewing fresh slick over his belly, hate fucked to climax by his cuckolded boyfriend. And then Stiles comes too.

By the time Stiles' dick stops spewing, in the same way his cock just emptied itself, so is the rest of him. He’s exhausted, his rage and anger are gone. Forgetting he might still be being recorded, Stiles slumps back and dry heaves. While he's air vomiting, Derek slides out between fatty's thighs, face still just as wrecked with cum and dirty ass juice as it was before.

He's just in time  to see his boyfriend-- er… ex-boyfriend, zipping up and running out

John stares back and forth between the door his son just fled through and Derek. Derek who’s on his knees and already nudging the toe of his boot with his filthy head, begging for another fuck.

The Sheriff knows his son. They’ll talk later, once Stiles has cooled off. They'll work this out somehow. After all they navigated greater tragedies and came out okay.

Still, he doesn’t return to the slut at his feet, but toes Derek off him and nods to his deputies. He shuffles the fat man off the bed and back into his clothes Leaving Jordan in charge while his guys turn their attention back to Beacon Hill’s neediest citizen.

 

 


	2. Cheating Derek II: The One About After the Prom

_Now, I’d of been happy to end the story where I did. For me that was as good a place as any for this dirty/bad/wrong romp to stop. But I got a request from Icy for another chapter to kind of wrap things up and show the aftermath of the prom debacle because he latched on to the wee bit of plot in this whole filthy ramble. Plus, I think he was kind of hoping to see Derek debased a little more._

_So I decided to take this on. Besides, I know there’s a lot of you out there that want to see Stiles get justice and the cucks who wrecked his world get served._

_Jluis for one. And oh my hell, but ferocious Thefujoshi, for another._

_I mean, you should check out Jluis’ comment; they practically wrote the epilogue there on their own. Which I loved. (In fact, I think you should all rally and encourage Jluis to flesh it out as a spin off. I’d read it!). But they’re a bit more violent than I tend to lean: I’m more of a fucker than a fighter._

_Not that everyone who broke Stiles’ heart doesn’t deserve a righteous thrashing._

_And man, after reading Thefujoshi’s rant, although it pleased me to no end, that little guy’s gonna kick my ass for this for sure. Sorry to disappoint you, dude. Having said this, I’m now going to offer my resolution. Keep in mind this is “porn world” and thus the rules of reality are “loose” here at best. HA!_

_But anyways, this is how I would have things play out…_

* * *

So the night of the prom, of course Stiles is fucking DESTROYED! He’s devastated, wrecked, on the edge of suicide, because, as if it wasn’t enough what happened at the dance and at the hotel, well, he ran home and started tearing the house apart. Torturing himself by looking for all the clues he missed about his dad and Derek’s relationship.

And you all know he’s a smart guy and the first place he’s going to look is John’s computer.

_And there it is._

Derek laid out in all his photographic glory/disgrace.

Yep, Stiles sees everything. But it’s the images of a fucked out Derek wrapped in his very own bedsheets, the ones that are on his bed that very day, that pushes him into full out crazy. He downloads every pic, every clip, onto his own external hard drive and then crashes his father’s computer. But it isn’t enough. He trashes it too.

And then he goes on to rampage through the house.

By the time he’s done his tux is in shreds, every frame holding a pic of him and his dad is shattered. Dishes are smashed. He takes a trauma induced diarrhea shit in the center of John’s bed just for good measure!

_Fitting, I think, after the crap his dad did in his._

Stiles packs his bags then, grabs a few pictures of him and his mom to take with him. He’s sweaty, snotty, sobbing and spent when he exits what once was his home. Throws his house key into the bushes as he climbs into Roscoe and heads over to Scott’s house.

Melissa of course, takes him in with open arms. She’s furious, righteously so, but not just on Stiles behalf. She and his dad had been dancing in and out of the “friend zone” for ages; had reached that “benefits” place as well. Yeah, you can imagine just how pissed as shit she was to find out John had been dipping his wick into Derek Hale while she and he had been intimate and, she’d thought, _exclusive._

_Ol’ John broke a few hearts that night._

After prom night Stiles weeps for a week grieving everything he’s lost. He spends the week after that one all but catatonic. He keeps his phone off. And if he stays in his bed wrapped in the Star Wars sheet he brought with him from the house, no one dares ask him why.

* * *

_Now that I’ve laid out that bit o’angst,  I’m gonna skip to two years later…._

Thank god Scotty and Melissa were there for Stiles after that night or he would have really hurt himself for sure. Though it’s questionable whether he would have ever been able to inflict the amount of pain on himself his dad and Derek had.

By now though, the biggest part of the gut wrenching, soul crushing heartache has faded. _Or so he would tell you._ Stiles would also tell you, despite how his prom night disaster wrecked him, he kinda got the last laugh in the end.

You see, after the “incident” the school brought in counselors and dealt with the angry parents.

Danny and Jackson, meanwhile, got expelled for what they did. Stiles himself got off pretty much Scott free, even though he was the one who installed the cameras in the first place.

_Guess everyone thought he’d likely been punished enough already just by the circumstances._

Though he didn’t get  thrown out, Stiles pulled himself out of school anyways. Like it hadn’t been a bitch trying to concentrate in his classes before that all went down. Melissa understood and continued to support him. She was a goddess to him in those dark hours, ruling a world where Derek and John had been excommunicated completely.

_Stiles was all for that._

So, he finished his courses online. But while he was working his way through those last months of school, he also hired a lawyer. Got a tall drink of water named Sam Winchester, out of Stanford, to represent him in an anti-bullying/ personal and emotional trauma trial.

Which he won.

It helped his case greatly that, before they got fingered for their little prom prank, Danny and Jackson were stupid enough to post the video to PornHub too.

Theses days Stiles supposes that he should kind of be grateful for that. After all, the feed at the prom had been cut off before he was captured on camera fucking the shit out of his cheating bastard boyfriend. So it wasn’t like it was his balls on display.

Not to mention that trial made him a hell of a lot of money. Ruined Jackson and Danny’s families with the payout to boot. Danny got disowned and Jackson’s family forced him to enlist. Shipped him off to bootcamp where his attitude pissed of his regiment so much they put him in the hospital for a month from a shit kicking.

_Does Stiles feel bad about any of this? No. He does not._

_And after two years of therapy he can now say this with resolve._

So once the case was resolved and Stiles had a couple million in civil settlement payouts stuffed in his bank account, what he did was take that money and go to the College he really wanted to, without having to worry about scholarships or asking anything of his father. Which was a blessing for a few reasons. The main one being he still sure as hell didn’t want to be put in a position of depending on his dad for anything ever again.

Of course, while he still feels this way, the sharpness of it has dulled somewhat. At least that’s what he tells his shrink every time he sees her. And that he’s actively working on forgiving his dad for betraying him like he did.

_Working on it. Though not really succeeding._

Yeah, thing have changed some between he and the sheriff. They exchange phone calls sporadically (very). When they do it’s mostly small talk.  Their conversations are stiff, but they’re more or less cordial now.

Originally, he was NEVER going to forgive his dad, but John caught him one day on the streets, like a year later, literally begging for a word. Stiles slipped in his resolve feeling that old familiar worry at the poor color in his dad’s face and the reappearance of the alcoholic veining along the sides of his nose. It was a terribly awkward exchange and when Stiles asked his pop on reflex how he was eating and John actually started crying…

Sue him for being a sap. 

But usually the Stilinski men took all their feelings and stuffed them into that lone laundry sock tucked away in the back drawer of the dresser to be forever ignored. So those tears got to him. Momentarily undermined his anger. And they moved on from there.

Before you go getting all up in arms about all of this, know Stiles still hates him in no small measure. But again... Those tears…

Still, the rare times they do exchange words, he doesn’t ask after his father’s diet anymore. And he’s never visited his dad for vacations. He bunks with Melissa when he visits BH. Scott too, if he’s home at the same time. 

Stiles is so super grateful he’s a free agent ( _like forever now, if he’s careful_ ) when it comes to his finances. Especially since, if he ever _had_ needed his dad’s dollar support he wouldn’t have gotten any.

John got canned, fired, thrown off the island, immediately following the video. 

_For “moral turpitude,” the city council called it._

This wasn’t so much about him and his deputies fucking Derek. They were all of age and _clearly_ consenting after all. And for apparently everyone but Stiles, Derek already had quite the established rep as the town bicycle.

It was more that the sheriff and his guys fucked Derek while they were on duty.

Oh... And that they involved an apprehended alleged criminal in their debauchery.

Although from what Stiles learned eventually, the guy said he had such a great orgasms with Derek, not only did he not press charges against the department, but he also didn’t even mind doing the minor jail stint he was sentenced to.

Or at least, that was one narrative he got on the post-prom events.

The other story surrounding the hacker ran kind of along these lines, but carried the added twist that the the guy agreed not to press charges if he could fuck Derek in the ass before he was locked up.

_I mean, once he had a taste of Derek’s mouth on him, the pull of Derek’s other pussy was overwhelming._

The tale went that the station (and Derek) was only too happy to oblige him, in order to get his signature on the release and non disclosure forms.

So, with cyber thief squared away,  John stepped up as the leader and claimed responsibility for his troops.

It was the biggest scandal Beacon Hills had seen in awhile, _if_ one discounts all the supernatural shit. The sheriff wrangled it somehow so that his team largely just got a temporary suspensions. And the city begrudgingly accepted this. After all, it wasn’t like Beacon Hills was a thriving metropolis. And up until John had been appointed to office, getting people to stay on the force with all the local “strangeness” had taxed the department for years.

Still, not everybody involved in the “incident” hung around despite the minimal professional consequences. Some guys’ relationships broke up because of the video. ( _Duh._ ) Others left town for the benefit of their intact but mortified and humiliated families.

Parrish had stayed on though, and now he was Sheriff. Doing an okay job by all accounts Stiles heard. Not that he knew much more than this, since he tried to avoid the man like the plague on the rare occasions he went back. His reasoning on this had proved sound after he ran into the former deputy one night about six months ago when he was in town.

Parrish was drunk and tried to apologize. What he said when he did this though…

_Well, we’ll get back to that later._

Anyways, Stiles had returned to town to get some repairs made on his old house. He still could barely stand to go inside it, but he’d bought their home after John lost his job and had to declare bankruptcy. It wasn’t an easy decision to make and he’d thought seriously about letting the bank take it.

In the end though, Stiles just couldn’t let go: Even though it had been totally desecrated the place held too many memories of his mom. So it it just sits there now, vacant, until the pull of old blood calls loud enough for him to have to go back and quiet it.

His dad left Beacon Hills too, not long after that crying scene. You see, by then he’d lost everything. Stiles is fine with this. Makes it easier to see Melissa or visit his mom’s grave. And there’s no way he’d have let his dad back into his house.

Not that John would have ever had the balls or lack of pride to ask for that. Besides, nowadays the Sheriff had picked up the pieces and was finally doing alright for himself again. Had a little place outside LA and his new business venture was going gangbusters.

“What was it?”you might ask.

_I gave you kinda a hint in that last sentence. HA!_

Well, it was another reason Stiles still kept contact with his pop minimal. You see, John made the brilliant decision of turning his lemons into lemonade and so, he had started working as a manager for adult film stars.

Yeah, once Danny and Jackson put that video up, the show he and his guys put on caught some attention for sure.  But it was Derek who really catapulted their clip into the stratosphere. And can you blame the world for responding like it did? I mean, here’s this buff, built, gorgeous, green-eyed god, the paramount of physical masculinity, weeping like a little girl ( _no disrespect intended ladies_ ) because he just can’t get enough cock.

_Yeah, the internet loved Derek._

Viewers couldn’t get enough of how needy and wanton he was. How willing he was to get degraded. They loved seeing the pinnacle of male perfection reduced to nothing but a few voracious holes. Loved, loved, loved seeing him beg for cocks, for fists, for cum and piss, and shit.

_Come on, I mean, who wouldn’t go apeshit over this?_

So offers started pouring in for Derek to make more porn. Of course at first, he couldn’t bother to try and negotiate his sudden fame. No. Not when all he could think of was getting his next fuck fix. Because after that night something broke within him too, it seemed. He went kind of crazy. Became even more insatiable.

But eventually he did do a few movies. Got paid almost nothing too. The producers took advantage of his cum-frantic state. At least, until John stepped in and started managing his fucks.

_The Sheriff just couldn’t shake that possessive streak he had for his old station bitch, it seemed. (Or maybe he felt responsible for Derek’s breakdown)._

Anyway, John snapped a leash on Derek. Once things got going he even hired a couple of his old deputies for the movies.

_The fans seemed to love the continuity.I know I would. Growl.  
_

Their resulting “Prison Bottom-Bitch” series even swept the prizes at the Vegas Adult Film Awards last year.

_Now don’t get me going on the story possibilities of cumslut pornstar Derek. Talk about a digression! Because the fic potential here alone is endless.._

Of course, Stiles still feels super conflicted about all of this. Not just because his dad is shacked up with Derek making sure his golden goose sleeps occasionally and stays hydrated, but also because his father is still fucking Stiles’ “perfect” ex boyfriend (sometimes on film too).

Though if pressed to be honest, _I mean really squeezed…_ Stiles’ would eventually admit there’s another layer to his struggle there. Because he sometimes ( _Okay, like a lot_ ) jerks to their movies.

_Yeah, he and his counselor are working on that one still._

These days though, Stiles doesn’t push the issue about his dad’s continued connection with Derek anymore. Although he still never responds when John tells him “Derek said to say hi too,”  despite the quiet plead in the man’s voice.

Because he’s past all that.

_Liar_

And because while his dad sounds worn out during those rare conversations, and occasionally a little drunk, he sounds kinda content too.

_Fucker._

_Sorry, that last one just kind of slipped out._

But there’s one more reason Stiles has chosen not to make a big deal about the fact his two greatest betrayers are shacked up outside LaLa Land, still screwing each other and living days and nights of endless dick.

And it’s not because of the counseling he’s received. Or the fact college really opened his eyes and his mind. See, he downed gender studies and sex related courses at the university like they were curly fries.

_Post-traumatic growth his therapist called it._

No, it doesn’t matter that he understands the human creature was never really designed for monogamy, or that polyamory works for some. And he knows about sex addiction and the prevalence of bisexuality.

_Has a great boyfriend and a great girlfriend of his own right now, as a matter of fact. Thank you very much._

He’s done more than just read too. He’s been to dungeons, experimented with fetishes of all sorts. Tried figging, splooshing, pet play, age play. You name it. He’s done it from both sides. On the other end of the sexual spectrum he’s come pretty far ( _pun intended_ ) with his tantric mastery too.

Yep, ask his lovers and they’d likely tell you that these days Stiles Stilinski has become a master sex ninja of sorts. But while all this knowledge is helpful, it hasn’t changed how he really feels.

So, no. The reason Stiles’ has been peaceable with his transgressors, even more so lately, is not because of his expanded horizons, but because he has a plan and has been biding his time.

The basis for his revenge was there along while he was honing his skills, though he didn’t realize it at the time. As was the seed of his scheme poking its little green head out of the black soil of his heartache.

Then Parrish gave it a shot of “quick grow,” and suddenly it bloomed.

_This is where we loop back around to that night at the bar and Parrish’s drunken apology/confession, I mentioned earlier._

You see, Parrish told Stiles in the midst of his infinite slurred “sorries” that while that night had impacted them all, outside Stiles, it had impacted Derek the most. The fury of that fuck, the drive of Stiles’ thrusts, the transmission of his feelings through his cock: it was a pounding like none Derek had ever experienced.

And once Derek had had that, he couldn’t forget it. Parrish even had the balls to complain, before he caught himself, how Derek wouldn’t shut up about it. Oh, the he remained a wolf of a few words, but after that night, you could bet when he did talk is was to lament the loss of Stiles magic cock. Sometimes even in the middle of when other were being kind enough to fuck him.

Yep, after that night Derek had become voracious. A true bottomless hole. After the high of that fuck, the pulse and the pound of it. Nothing… BUT NOTHING… gave him the same feeling that Stiles’ fuck had.

No matter how big or how many, every experience after just left him craving it more.

At the time Stiles had pretended to shrug this information off like this didn’t effect him, didn’t make him immediately hard in his heart and cock both. Yeah, he just made a bland comment about “Derek’s loss,” cooly accepted Parrish’s apology for about the dozenth time, and excused himself.

But once he got back to school, he locked himself in his private dorm room and brought out the video from prom night.

I know, I said the feed Danny showed at the prom cut off before Stiles became visible. But _Stiles’ feed,_ the one running from the cams to his phone was rigged so that it also went directly into a file on his computer. And the cams at the hotel that night had caught the entire thing. THE ENTIRE THING. It kept recording even after Stiles fled.

About three hours of video, all told.

Stiles had never looked at it. The thought of it made him sick for months. And he couldn’t tell you just how many times his finger had hovered above the delete button ready to press. But he hadn’t deleted it. For some unknown and likely highly masochistic, reason he’d kept it.

And that night he viewed it. Finally.

It took him forever to get through it the first time, cause he kept vomiting. He simply couldn’t hold back the bile that rose in his throat seeing the night that had haunted him since it happened brought back to technicolor life again. The second time he viewed it, he didn’t puke. No, that time he jerked himself raw. Watched himself pound Derek and, remembering in spite of his anguish the hot mess of his ex’s glorious hole, he came until he came dry.

Once he got all of his fluids expressed. Stiles went into study mode. This time he approached the footage like it was a lacrosse reel, back when he (kinda) played for the team. He missed all his classes that day reviewing it.

He gets it finally: what Parrish was talking about. It was subtle at first, but after watching the video over and over after awhile it seemed so blatant. When Stiles slid into him and started pounding, the shift started with a slight blush that darkened Derek’s hairy chest, makes his nipples bud even tighter.

For sure there was something there in that fuck and it was more than just Stiles’ fury. And his mind recalled a lecture by Deaton about werewolves and “true mates.” How it was extremely rare for a wolf’s true mate to be human, but it happened occasionally. And by the time Stiles watched the fucking through for the sixth time, saw how Derek’s body responded even as he had his tongue in the hacker’s filthy hole,  Stiles is  convinced of it.

Now unlike some would have you believe, “true mates” doesn’t necessarily mean monogamy. True werewolves mated for life but that didn’t preclude them only having sex with said mate. And with a cumslut like Derek, it was clear that would certainly be his case. But what a true mating did mean, however, was that once sex had been totally reciprocal _(and in guy on guy sex this entailed both dudes bottoming)_ sex after that would only really ever feel totally complete with the werewolf’s true partner.

_Note that I said “werewolf” there._

Because what Derek didn’t know and Stiles learned doing more research later, was that this “true mating” didn’t affect non-were’s in the same way. Sex remained “just” sex for a human and for a human too, the emotional bond could be broken. It was difficult, true, but as Stiles had learned only too well, while excruciating it wasn’t impossible.

And after watching the video ad nauseam, Stiles truly understood how deeply nympho Derek was affected. Even more, Stiles realized once he’d shot his seed into him, cementing their bond, it was like sexual crack for the cum hungry werewolf. One hit from Stiles pipe and Derek was an addict. Not that either of them realized what had happened at the time.

But anyone who knew the truth would have easily seen, once Stiles left, how immediately greedy Derek grew. The way he whimpered and whined, increasingly unsatisfied with every new load he took. By the end of the video, Derek was pulling refractory and every power bottom move he could, until the the exhausted deputies cuffed him hand and foot to make him stop.

Once Stiles understood this, the power he had and what this made possible,  he couldn’t stop replaying the video. At least not until his worried boyfriend Xander broke into his room and caught him cumming and crying to the footage, wearing his spunk stiff Star Wars sheet like a toga.

Xander immediately called over Stiles’ girlfriend Buffy and once they got him cleaned up and back in control of himself, he sat them down and told them the whole sordid story and about how he needed to get revenge.

Yep. That bit he’d said about “Derek’s loss” to Parrish… Now Stiles knew that much was true and once he saw the vid and caught the true mate bit, he’d decided in that instant he was going to make Derek, the horny bastard, feel this loss anew. While this time turning up the volume about a thousand.

He shared his plan with his lovers. That both had a bit of an understanding about the supernatural was part of what made them perfect for Stiles, and that they were both game for it made them even more so. In fact, Buffy and Xander both loved him enough not just to be supportive, but wanted to help however they could.

See, that’s the benefit of open communication and open relationship. And if Derek had trusted Stiles enough to practice this, he might have been able to avoid his impending collision course with destruction.

**Notes for the Chapter:**

> I know Icy asked for one chapter, but you're getting two. So next Monday, Cheating Derek III: The One About Stiles' Revenge and Derek's Destruction.
> 
> Stay Tuned.


	3. Cheating Derek III: The One About Stiles' Revenge

_Okay. So here’s the wrap up to this sordid series._

_For now, anyways... Since Benn_Xaiver forwarded a request to see the fat hacker have Derek’s ass, and IcyCryos made a private plea for a peek into Derek’s early porn forays before John stepped in._

_Not making any promises, but if the mood strikes, these guys might get their wishes. We’ll see. The problem is there’s so many glorious ways to defile our favorite werewolf and only so much time._

_Wish I could get a grant to just write fuck fics. I wonder what a “go fund” me for that would look like. Heh. In a perfect world…_

_Sigh._

_But anyways, back now to an equally imperfect fictional world where sweet boys get grossly cuckholded by their impossibly hot, slutty, older boyfriends/true mates._

_________________________

So once Stiles spills his story, he finds his new lovers more than righteously indignant on his behalf. Buffy, Stiles knew from the start, had a strong sense of right and wrong. Not only that, but she’s a total badass and immediately ready to thrash Derek for her beau.

Xander isn’t so aggressive. More a follower. Kind of hapless, (which Stiles totally relates to). And while Xander isn’t anywhere near the hotness of Derek, he has one quality the were-slut doesn’t; it makes up for that smoldering constant five o’clock shadow and washboard abs and makes Stiles love him immensely.

Xander is faithful.

Like, you looked up the word “loyal” in the dictionary, his picture would be there right under the definition. _He even happily let Stiles put him in chastity for six months after they first got together, just to soothe his Derek-induced paranoia about fealty._

Yeah, so Xander is down with whatever Stiles and Buffy want to do. Which it turns out is quite a lot.

With his lovers’ blessings Stiles goes into research mode. _Not that he hadn’t kind of quietly cyberstalking Derek for a while already._ So it doesn’t take too long for him to figure out the best way to get his revenge.

His final plan goes like this…

Derek has become increasingly insatiable since that fateful prom night. His two ravenous pussies continue to need despite his porn work and John. (After all, there’s only so much Viagra a guy the sheriff’s age can take; even when his bitch pulls refractory like it’s going out of style). In fact, Derek is such a nympho now John even has to keep him locked up in a mountain ash cage at night to prevent the slut from sneaking out and sharing his moneymaker for free.

_Something that has happened more than you’d think even with the cage._

This aside, a while back smart guy John hit on a scheme as Derek’s porn sales and his libido continued to climb: he starts hosting gangbangs for his star and filming them. Each successive one adds a few more cocks into the mix: five becomes ten, twenty-five guys eventually edges up to fifty. And by the time Stiles is ready to carry out his plan, his dad has just scheduled Derek for his landmark ‘One Hundred Man Fuckathon’.

_Crashing in on this golden milestone is just too perfect for Stiles to pass up._

Now, of course there’s more to this. I mean, it’s not like Stiles can just get in line with Derek’s other fuckers. There’s history there. And his Dad isn’t likely to let him participate. Or maybe in a moment of guilty remorse John would. Regardless, Stiles isn’t about to find out.

What he does find out however, after some deeper research, cruising some covert, backdoor websites, is that his dad has fallen even farther down the ladder of respectability than he’d previously thought. You see, John is not only Derek’s manager at this point, he’s also become his pimp.

At least that’s what Stiles concludes when he stumbles across the site where anyone can post a bid to be one of Derek’s fateful one hundred fucks.

_Starting bid: An insulting $100._

When he discovers that the highest bidder not only gets to be the first to taste Derek’s cunts that night, but also will have an allotted amount of alone time with the star of “Bad Dog” Productions Inc. Well, everything quickly falls into place.

He makes an account for Xander and has his boyfriend bid. Since money is hardly an object, of course Xander wins the auction. Derek’s holes sell for a cool fifteen grand.

_Funny, considering Stiles once thought him priceless._

Anyways, the night of the one hundred man march on Derek’s ass arrives. Stiles, Buffy, and Xander hop a plane to LA, rent a car and travel to the production site.

 _Well, almost._ _More like Xander drops Stiles and Buffy off a half-mile away and goes on his own to the house where the shoot is taking place._

It’s on the outskirts of the city. An older neighborhood, once rich but that’s since slid down the economic scale. The house is in fair shape though. Has a pool in the back. Big brick outdoor grill. And a screened in porch where the gangbang’s going to take place.

The way the scene is decorated, it’s clear John’s going for a barbeque theme here. The guys filmed hanging out around the grill, eating prime cuts and drinking beer while they take turns enjoying another fine piece of meat:

Derek, bound, laid out on a picnic table under the awning.

The place is on loan from an eighty year-old geezer, John explains, as he’s walking a horribly nervous Xander through the house. The guy traded the location to be in the first twenty of Derek’s fucks. John chuckles and offers conspiratorily that he hopes it doesn’t kill the old coot, the thrill of sinking his old wrinkled dick into such a fine ass.

For the auction winner, however, there’s no picnic. Instead Derek’s pimp/manager leads Xander down one of the first floor halls to his own private feast. Stops outside a closed bedroom door.

John lets him know Derek’s been set up exactly the way he asked for.  Explains again, while Xander is signing the release forms, how there’s cameras set up all over in the room, programmed to run for his purchased ninety minutes. Because while his fifteen K bought him some privacy and a chance to indulge his personal kinks, John’s not about to lose that footage.

The last thing John offers, _and he goes all stern, old law man on this_ , is that Derek can take most anything ( _he doesn’t go into details; not all the world is werewolf wise, after all_ ) and likes most everything.  He does warn that he’ll be close by, however, and if things sound like they’re getting out of hand, he’s more than willing to step in.

Xander’s involuntary gulp and cringe seem enough to satisfy, so with a hearty clap on his shoulder and a sighed “have fun,” John turns his slut’s ass over and goes out to do an equipment run through with the crew.

When Xander enters the room he can’t help but gulp again. This time at the sight of his boyfriend’s ex.

_Who wouldn’t? I mean, get this set up…_

The room is large with a bed and a couch, but Derek isn’t laid out on either of these. He’s lying bare ass naked on a massage table that appears to be bolted into the floor.

Xander can’t see Derek’s face: per Stiles’ specifications he’s got a sensory deprivation hood on. The many-zippered, black leather mask encases Derek’s head, rendering him blind, deaf, and as long as the mouth stays zipped, more or less mute as well. The hood he’s wearing even has a special filter fit into the nose, so that while Derek can breathe, he’s bereft the benefit of scent.

But what really catches Xander’s attention is the visible rest of Derek’s body.

_I mean, holy hell…_

The dark hair on his forearms and lower legs is lush, the signifiers of pure high-testosterone masculinity and a beautiful contrast to the baby smooth skin of his waxed, bare torso (minus a carefully coiffed pubic patch).

Not to mention that since taking up porn, for those few hours Derek’s not getting fucked, he’s working out constantly, trying to burn off the heat of his “cock fever.” As a result, he’s even more ripped than before. How he’s been bound just highlights the incredible definition of all those pumped up muscles.

_And the way Derek has been tied..._

He’s got a thick, black leather collar fastened around his neck. _This detail is important._ He’s flat on his back on the padded table, his knees pushed up almost to his ears. You see, his muscular arms have been wrapped around under his thighs, his wrists chained, each one, to a heavy steel D-ring on the sides of his collar.

He’s a presenting pretzel, helpless, legs handcuffed by his own arms, his ass accessible to anyone who wants it.

And as if that wasn’t enough of an invitation, out of his bald, rosy-hued pucker, the end of a black silicone slut plug is on display, signalling that this ass wants to be toyed with.

Now, there’s tasks Xander should be doing, but it’s hard for him to pull his gaze from Derek’s hole. Lube, white and thick as Crisco is oozing out around the plug as his hungry cunt clenches rhythmically milking it, trying to cum. Once Xander does finally look away, or at least higher up, he’s confronted next with Derek’s junk.

John thoughtfully bound his bitch’s heavy balls. Wrapped them in a black cord, separated, high and tight so they won’t get in the way, and to keep Derek from coming too much. _After all, he doesn’t want to have to stop his shoot because Derek’s “man milk” bag has run dry._

Derek’s balls are already swollen and purpling, skin tight like ripe plums. The ex-sheriff ringed his cock at its tastefully man-scaped base as well. The Prince Albert-pierced monstrosity that’s Derek’s dick lays red as a dog’s rocket, hard, and leaking clear pre-jac, onto his curled, rippled abs.

Seeing this bound god stirs all Xander’s insecurities. _I mean, what’s he after Stiles has had this?_

It makes him feel a little mean. _Well, meaner._ After all, he loves Stiles and this cumslut wrecked him. So, Xander can’t help but step up and tweak the plug. Grin bitterly as Derek jolts in surprise, then grunts like the little fuck piggy he is and starts desperately wiggling his ass, trying to grind his eager hole against the plug in his unknown rival’s hand.

Xander’s never seen such a wanton slut in his life. He can’t help it. He starts fucking Derek with the plug, _just a little bit_ , mesmerized by the way his rosy cunt slurps at it. He gets so caught up in this sight he jumps and make a less than manly noise when he hears the tapping on the bedroom window.

Ignoring Derek’s muffled groan when he stops toying his ass, Xander lets Stiles and Buffy in. They crawl through the window, no problem. _Clearly John’s gotten lax about security since he’s left the force._ They drop the duffle they brought between them on the floor.

Buffy is all business, barely looking at Derek. _They’re on a schedule after all._

In moments she strips down to just the harness she has on under her clothes. She goes into the duffle next and pull out her extra-large “Nocturne,” bad dragon cock. Not only is this bad boy a solid foot long, with a wicked curve, ridges, a head seven inches in circumference and a knot at the base that’s ten _(true story)_ , but it’s lavender color matches that of her harness and both look amazing against her pale skin.

She steps up while Stiles and Xander are still pulling out of their clothes. Lands a hard smack on one of Derek’s swollen pecs, follows this up with a wicked titty twister aided by the ring piercing his nipple that leaves him writhing, shouting behind the leather.

She shakes her head and shoots Stiles a pointed look as if to say, “this is the bitch that broke your heart?” A nod from Stiles is all she needs, and she gets to work.

If her hand is slightly smaller than most guys, Derek doesn’t have time to notice. Not with the way she lays down so many fast hard smacks to his ass, making sure to hit the plug intermittently and drive that sucker in deeper. After all, it’s that filthy hole they came to punish in the first place.

Now, don’t think she gets so taken with this that neglects Derek’s other naughty bits. She squeezes his already constricted balls and slaps his dick hard enough to make Derek scream in between warming his ass up. By the time she’s done the bitch is leaking everywhere: saliva bubbling out through the teeth of the mask’s zippered mouth, the leather of the massage table dark in spots from the pre-jac dripping down the sides of Derek’s belly and the lube melting out of his ass.

Good thing Derek’s hole is so greased, cause once his butt is glowing hot and bright she pulls the plug out of it with no ceremony. And Derek’s cunt hasn’t even finished its startled gasp when it’s gagged back up by the monstrous head of Buffy’s bad dragon pushing in.

Now this, Derek feels this immediately, in so many ways. But the most important is that his man cunt knows silicone from skin in an instant. And that’s not what it wants.

No way.

Tongue, cock, fist… it doesn’t care, but it wants hot flesh.

NEEDS IT.

_Not that it has a choice here._

Inside his hood, Derek starts to growl his protest, so it’s a good thing John has his slut’s bondage all sigiled so he can’t break loose. An even better thing when Buffy leans over him so that her breasts rub against his own iron-pumped man tits, because when Derek realizes he’s about to be fucked by a woman, he loses it.

_Maybe it’s a Kate thing. God, one can only hope-- and would someone please write that?_

_Okay, so back to the moment._

Buffy, rightly so, takes offense at this response. Pulls down a zipper on the side of the hood to reveal an ear tipped almost as red as the head of Derek’s suffering cock. Starts talking low and fast and dirty. She grabs the chains attached to Derek’s wrists like reins to keep her wild pony from bucking itself off the table. Uses these to hold him in place while she gets ready to break him.

It’s clear she’s anticipating her ride to the same extent Derek’s resisting it.

Buffy drags his ass to the table’s edge, pulling him deeper on to her as she rocks back and forth, still though, just the head of her cock inside him, torturing him even more mercilessly than the words that follow.

She says in a taunting tone how she can’t understand how someone with such a conscienceless cunt would be so sexist. Tells him she paid for his ass, so he can just sit back and enjoy it. Promises once he’s had a taste of her cock, he’ll know just how a “real man” fucks, and all those bio-boys will pale in comparison.

And then, she impales him. That dragon dives deep into his hot cavern and starts making itself right at home.

It’s impossible for Derek’s back to arch, the way he’s tied up. So, instead, his whole body jumps up off the table, twisting. That massive girth, the bite of Nocturne’s ridges, has him pleading in muffled gasps inside his hood.

While Buffy’s doing all this, with Xander wrapped around him from behind in a protective, possessive back hug, Stiles has been standing to the side, watching in awe. _And not at all triggered by seeing Derek again. Nope._ He’s definitely not so stunned that he can’t move when Buffy calls out for one of them to shut the bitch up so she doesn’t have to listen to him.

Given Stiles’ “ _unstunnedness_ ” it’s Xander who takes the lead next. Steps up and unzips more mask so that the lower half falls away revealing Derek’s impossibly angular, spit sloppy, stubbled jawline.  And that mouth…

_Oh, that’s a mouth made for cock if there ever was._

Derek is growling and gasping simultaneously, clearly unhappy and stuttering curses in between pleasured moans as Buffy finds her pace. Those ridges on her dragon rubbing him in _ALL_ the right places.

Seeing Xander step up she shifts Derek’s body while she fucks him so his head dangles off the table giving her boyfriend good access.

For all his earlier protests, Derek shuts right up when Xander presses the head of his cock to his lips. Desperate for flesh he opens his mouth pussy at the first brush of Xander’s flaccid cock, latches on and starts suckling like the slutty piglet he is.

Now, for all his goofy awkwardness, Xander does have a magnificent “member.” _Fuck, who comes up with these terms?_ It’s thick as a wrist and nine inches. And he fucks like a champ when he’s into it. Problem is, as hot as Derek is, right now Xander’s not.

_Like I said, loyal._

Of course Buffy notices and starts berating Derek, asking what kind of gay pornstar can’t get another guy up. Despite her harsh words and the fact it’s a chick fucking him, Derek’s bound dick visibly twitches and spits out even more precome. The more she demeans, the more fervid Derek’s mouth grows. His throat opens like a lotus and he takes Xander to his wilted root.

As masterfully as Derek sucks and slurps, hollows those high-boned cheeks of his, it’s not until Stiles steps up and starts kissing Xander that his boyfriend’s dick takes a real interest.

_It’s going to be a pretty picture later, that bit in the video. Stiles and Xander kissing, Buffy looking on with a fond grin on her face. Derek between the three of them, nothing more than a couple choking holes._

At that point Buffy’s still fucking Derek slow, plunging deep, stopping just short of the knot and pulling out at a languid pace to ensure he feels every curve and ridge of the dragon inside of him.

As she does, Stiles hands her a thick flat strap that she uses to punctuate each push and pull with a smack somewhere on Derek’s body. Xander moans into Stiles’ mouth as Derek’s throat constricts around him with every “Crack!” of the strap.

Stiles gives 95% of his attention to Xander, but he can’t help making little sideways glances now and then down at Derek, spitroasted between his lovers like a Luau hog. Xander’s cock in Derek’s throat, rhythmically pushing his Adam’s apple into even more prominence. The dragon is doing it’s work too, its snout visibly bulging Derek’s muscle-scaled belly as it roots around in his rectum.

Now Buffy is having fun. _Well, as much fun as one can have reaming the ass of her beloved’s cheating ex._ Still, she can’t help glancing down at her wristwatch. Seeing the time she picks up the pace.

Once she really gets going, she pegs Derek hard and fast and brutal.

Derek howls around Xander’s cock when Nocturne’s knot pops in for the first time. It punches his pucker like a fist. Buffy’s entranced watching the knot press and pull the ring of Derek’s sphincter. Xander’s close to coming, so he pulls out and once Derek can breathe he’s not protesting any more.

Nope, now he’s begging to have his “clit” unbound so he can come on Buffy’s cock.

And Buffy… She laughs at his pleas. She felt him tighten around her, knows he’s ridden that internal wave at least half a dozen times already. Even if he hasn’t been allowed to jizz himself.

Tells him the only dick coming tonight will be hers.

See when she ordered her Nocturne, _special made,_ thanks to the wonders of Stiles’ credit cards. She had a cum pump installed in her cock and she’s ready to go. She breaks up her boys’ continuing kiss fest with a low whistle.

Xander comes around behind her then. Grabs the hand-squeeze pump she’s got strapped to her thigh and clenches that pouch while his other hand pinches her nipples. Between that and the way the dildo has been rubbing her hard lady-dick just right, Buffy throws her head back and comes. Her hips buck forward hard, the nubs on the outside of the dragon at its base torture Derek’s taint, and its knot pops fully into him.

Derek’s greedy ass clamps down on it. His ravaged channel is flooded with cum-lube, heated by Buffy’s skin and his own fevered innards. But there’s more… And this is courtesy of Scott.

But there’s more… And this is courtesy of Scott.

_See, Stiles told his best friend/bro about his plot for revenge. Seeking absolution or dissuasion he didn’t know which. He was surprised when Scotty gave him his blessing. Without hesitation._

It seems even a happy-go-lucky, forgive-and-forget guy like Scott has his limits. Especially when they involve someone hurting not just his bro, but his mom.

_Yeah… any guy who can stand seeing his mom cry isn’t much of a man at all. Even less if he doesn’t try to make things better for her after._

So, not only does Scotty condone Stiles’ scheme, he adds his own two cents. And that’s how it came to be that Buffy’s cum-lube this night was infused with a couple extra ingredients: a little bit of wolfsbane and a more than healthy serving of pure ginger oil.

Now the bane was added to knock down Derek’s werewolf defenses. And the ginger oil…

Well, do you guys know about “figging”? It’s where you make an plug out of ginger root and stick it in someone’s ass. Burns like no motherfucker you’ve ever known and once it’s pulled out, that ass will take most anything in the hopes of quenching it.

Only in this case, there’s no plug to pull to stop the burn.

It takes a few moments to work. There’s a tingle first, then an itch, and then…

If he were a human, Derek would be on his way to the ER, showing up with internal chemical burns and an embarrassing story. But he’s not human, and with his healing slowed by the bane, what he gets instead is the fire that’s raged in his ass since the night of the prom goes from something you roast marshmellows over, into something that’s going to reduce the whole forest to ash.

Even with his werewolf magic, Derek is soon howling. And it’s about this time that Stiles starts waving his own dick less than an inch away from Derek’s grimacing, gaping lips.

Now remember, Derek can’t smell, but his tongue flickers out and it’s almost like it shares a snake’s ability to taste the air. Derek shuts up in an instant. The next thing Stiles knows is his ex-boyfriend yells “GREEN!” about three times.

It’s only after the silence resumes Stiles and his accomplices hear the heavy footfalls moving away from the door. Apparently his howls brought John in from outside to check on him. Derek, with his one uncovered, sensitive ear heard his daddy pimp’s approach and stopped him from breaking up their party.

_Interesting._

What’s even more interesting is the soft whine that fills the room soon after. Stiles has never heard such a needy sound.

And then the begging starts.

Blind and scentless, still half deaf, this doesn’t keep Derek from whispering a dozen “pleases,”  low and raw from his raw, cock-choked throat. When Stiles doesn’t respond the pitch of them grows higher. Soon Derek’s adds into his litany of pleases, “I need it.”

When this still doesn’t work he trying out titles, “Sir… Daddy… Master… ALPHA…” That’s when Stiles decides to shut him up and sticks his cock in between Derek’s begging lips.

_Well, not his cock exactly…._

See, Stiles has a nice dick. A respectable seven inches and a more than average thickness. And while he’s learned to wield this fleshly saber with the skill of a samurai, he wanted to leave Derek with something more to remember him by.

So, before heading out to LaLa, he made a stop through Beacon Hills, saw his old mentor, Deaton. Got himself a special potion. So now and for the next few hours he’s packing ten inches, and a girth slightly fatter than a can of Red Bull.

_Though with Derek being his true mate, truthfully Stiles dick could be thimble sized and as long as it was capable of cumming Derek would still crave it._

Anyway, the second Derek’s tongue hits the tip of Stiles’ enhanced cock… The moan he makes... _Well, that sound alone is enough to make a fanboy cum._ It’s absolutely orgasmic.

Stiles starts to pull away, and Derek goes immediately frantic. Chasing blindly after what was his fated cock chanting, “No! No! No! I need! I need! I need!”

And who’s Stiles to deny a guy in such dire straits? Well at least at the moment. So Stiles feeds Derek his cock, slowly. Inch by inch, making Derek wait no matter how much he wiggles and whines, no matter how much he drools or sucks or swallows.

While Stiles is doing this, Buffy pulls out of Derek. She’s rough and graceless, semi-pissed with her boyfriend’s seeming mercy. The sound that her cock makes popping out is squelchy, thick and viscous. A torrent of cum-lube and melted Crisco follows after, dripping from Derek's pussy.

_I mean, that table is pretty much ruined._

Now, I haven’t forgotten about that ginger oil. And believe me, neither has Derek. His hips thrust, his bound cock waggles ridiculously as he tries to air fuck the relentless sting out of his ass. Or, at least he does until Xander steps up, grabs his hips roughly and fucks into him. Catching Stiles gaze Xander holds it. And with every vicious thrust his look let’s Stiles know this fuck is only for him, regardless of the pussy he’s sheathed in.

Derek doesn’t know this though. And the were-slut is in raptures at the taste of his unacknowledged mate and the feel of frictioning flesh, rubbing the fire out of his cunt. He’s whimpering and writhing, all his synapses popping like fourth of July fireworks. An Xander, well the unabsorbed ginger lingering in Derek’s magic man pussy tingles and heats up his cock too. Not painfully, but enough to pulse even more blood into it, making it the biggest, hardest boner he’s ever had in his life.

Though it take some contortion, he and Stiles lean in over Derek and manage to find each other’s mouths. They both moan in how delicious the other taste, how wonderfully the cock holster they’ve got their guns in holds them. Beneath them Derek hears their pleasure. Maybe unconsciously he even recognizes Stiles’ voice.

_Though I guarantee you, his mate never sounded this fully pleasured when he and Stiles were together. Even though Derek was a more than adequate top._

Whatever it is, the sound, the taste, the being double teamed by two perfect pricks, it just turns him on even more. Derek’s entire body is flushed, fever hot to the touch. His ringed nipples stand erect on his heaving chest; pre-come weeps through the hole on the underside of his glands, around the heavy steel of his princely piercing; and he’s whimpering and whining enough for an entire twelve pack of starving pups.

When Stiles finally releases Xander’s mouth so he can really get to work, as he pulling back, that’s when he notices it. His whiskey-colored eyes blink drunkenly at first, but when he fully registers what decorates the inside of Derek’s left arm, his gaze immediately goes stone-cold sober.

It would have been so easy to miss, there at the top of Derek's tricep, almost obscured by the thigh it’s holding. The letters are on the smaller side, the ink is dark (though not dark enough to be new), and the script perfect.  

_Stiles_

_The font it's in is called “good vibes” in case any of you are typographers… or simply curious. Seriously, it's a real font. Appropriate for Derek, don't you think?_

The bottom falls out of Stiles gut when he see this name. His Name. The only tiny bit of ink, beyond his triskele, to be found on the flawless surface of Derek’s entire body. His breathing picks up and he knows the signs of a panic attack when he sees one.

Fortunately so do his lovers.

Buffy darts around to him, sharp eyes follow his stunned gaze. On the other end of Derek, Xander has stilled watching them. While Buffy assesses, Stiles’ freaks out and Xander waits. Derek, meanwhile, writhes between the cocks stuffing him, aware only that the magic motion quieting the eternal ache in him has stopped.

“It doesn’t matter.”

Just three words, but they’re enticing enough for Stiles’ whirling mind to pause. Buffy leans over and zips the slit, pushing Derek back into deafeness. To punish the way Derek whines unhappily around Stiles’ cock at this, she smacks his throat where Stile’s cock lays still and bulging enough to make him choke.

_Which given his total lack of gag reflex at this point says something._

It’s clear from Derek’s body language, he’s very unhappy about being reduced to a two-holed cock warmer, but he’s been trained enough at this point he takes her hint and submits, though his body quivers constantly.

Once she has the audience she wants, Buffy reiterates what she said before. “It doesn’t matter.”

“It doesn’t matter why or when he got it, Stiles. Whether it was because he missed you, or for penance, or so he could look at your name when he’s on all fours being fucked into by some stranger and wants to remind himself of what he lost. It doesn’t even matter if he got it without knowing entirely why, but because somewhere, deep in his subconscious his body recognized you as his true mate.

“It doesn’t matter Stiles, because it’s been over two years now. Two years since he fucked you over, broke your trust, broke your heart, and in all this time… If he’s so man-stipated he couldn’t face you… Couldn’t have just once, picked up the phone, dropped you a note, even sent a text… Reached out in any way…

“Babe, true-mate or not, this bitch does not deserve you.”

“And he deserves this…” Xander pipes up now. “You’re far too wonderful to have to put up with this kind of shit.” He waves his arms around indicating the whole sordid scene. “Please, Stiles… leave the past behind and make a future with us. With people who love you enough to choose you.”

Buffy’s pragmatism, Xander’s heartfelt plea, and the fact he can see on both his lover’s faces that they truly don’t want to lose him. Stiles' mind flashes to that night at the hotel. The way Derek turned right back to the fat hacker’s cock. The fact no one chased after him when he fled the scene. Buffy’s reminder of two plus years of radio silence.

The panic in him falls away and with it whatever tiny trace of his previous bond with Derek remained. He blows Xander a kiss across the table and turns to bestow some serious lip lock on Buffy.

He is finally, truly, completely free.

And still completely hard…

So with this, Stiles starts fucking Derek again. Xander resumes too, grinning at him from across the table. Fully able to enjoy himself now, Stiles revels in the fit of Derek’s throat, the way his balls rest on Derek’s upside down nose. He loves the tickle of hot breath on his sac as his ex struggles not to suffocate.

It’s just shortly before he’s about to come that Stiles decides it’s time. He pulls his cock out of Derek’s gasping mouth and unzips the back of the hood, pulling it off. And it infuriates him to no end that regardless of the fact he’s been stashed in tight leather and sweating for three-quarters of an hour, Derek’s wet hair still looks fucking sexy.

When the hood comes off Derek blinks his eyes. It takes a couple minutes for them to adjust to the light even with his werewolf reflexes. When he recognizes it’s Stiles standing over him. Well...

_Price of tonight’s private fuck: $15,000.00… Look on Derek’s face: PRICELESS!_

All the cool snarky greetings Stiles has planned flee him. Derek is gawping like a carp but the moment he utters the first “S” of Stiles' name, Buffy steps in and silences him with her cock. The massive head of Nocturne, it turns out, makes a great alternative to a ball gag.

With a few silent signals and some skillful teamwork, Buffy keeps Derek gagged while she and Xander lower the table and flip Derek over onto his stomach.

Buffy takes the reins again. She’s a pretty accomplished dominatrix when she wants to be. She orders Derek to suck her cock, Xander to resume fucking Derek’s cunt, and Stiles to slide that beautiful dick of his into her pussy.

Stiles steps up behind and obliges, reaching around to play with her tits just the way she likes.

Buffy isn’t overloud in her pleasure, knowing that in all likelihood John’s nearby, somewhere outside the door. She’s vocal enough though, expressing her pleasure, praising Stiles’ cock. Using Derek’s name to tell him pointedly just what he’s missing out on. All the while her cock fucking into him as Stiles fucks into her.

She gives not two shits about Derek’s tears, the soul-wrenching look in his anguished green eyes, or the way his throat chokes on the sobs she keeps fucking back down his throat as she shudders through not one, but two squirting orgasms.

And no one in the room seems to hear him howl around her cock when Stiles shoots his first load deep into her pussy and the smells of his cum hits Derek’s nostrils.

_Man, if these guys thought Derek was a slut before…_

His pupils dilate to the point he looks demonic and his need for Stiles’ cum makes him absolutely frantic. It takes all three of them to subdue him. In the end, Derek ends up reconfigured, his bonds changed up. His ankles now bound to thick leather straps fastened around his thighs, keeping his legs bent.

Xander chains the cuff of each ankle to one of the legs of the table as well, so that Derek’s ass hangs just over the end. Buffy pulls her dragon out of Derek’s mouth and before he can say anything Stiles is there locking his ex’s mouth pussy up with a dildo gag. He fastens this around Derek's thrashing head while Buffy clips the cuff of Derek’s wrists together and tethers them to the other end of the table leaving his muscular arms stretched above his head.

He stills almost instantly when Stiles starts speaking. “You could have had this you know.”

Stiles dips his fingers between Buffy’s legs and she audibly purrs as he fingers her there before pulling away to wave a hand dripping with cum before Derek’s dumbstruck face. He holds his fingers inches away and Derek’s whole body vibrates, leaning as much as its bonds allow towards the magnetic pull of “mate.”

“You could have had this too…”

Stiles sighs as Xander slides up behind him and works his cock into his ass. Stiles positions himself so Derek can watch him and Xander do a standing fuck. He wiggles and works his boyfriend’s sweet dick like the true power bottom he is with Xander making rapturous noises behind him.

Derek, trussed as he is, watches from the side and silently weeps.

Cries harder still when Buffy drops to her knees in front of Stiles. Takes his cum-covered fingers into her mouth first and lick them clean. Then downs Stiles’ enhanced cock like a sword swallower. Moaning around him like it’s the most delicious thing she’s ever tasted. Sucks Stiles so completely even Derek’s werewolf senses would come up empty trying to find any trace of his jizz.

Once Stiles is fully hard again, _(and god bless Deaton, because his trick also gave Stiles super refractory)_ ,  Buffy slips off him. Stiles shudders and Xander groans and comes inside him, eyes locked on Derek, holding his tear-filled gaze.

Xander disengages. Stiles kisses him and Buffy both deeply before he walks around the table between Derek’s open thighs.

“And you could have had this…"

**Notes for the Chapter:**

> Did I say this chapter was the wrap up for this fic? 
> 
> Yeah, well, I lied. 
> 
> I'm a tricky sucker that way. Totally untrustworthy.
> 
> So there's one more chapter for this ticket to hell. Hope you'll stick around and join me for the ride.
> 
> And btw... You commenters are fucking awesome. Beautiful bastards the lot of you. Seriously.


	4. Cheating Derek IV: The One About the Gangbang

**Notes for the Chapter:**

> Did you notice that this is now a five chapter fic instead of four? Yeah, once again I've led you on about this story ending, but then I've always been a fan of edging. Heh.
> 
> Jluis, this is for you, Dude. Had to break the chapter here or you'd be waiting another month for it. So, you better write something nice in the comments.

_So, this is the continuation of this terrible tale of lust and betrayal. It’s a hell of long way from the fast, nasty oneshot I intended. Thanks guys, for making me stuff this with so many unplanned twists and god damn feels too._

_And thanks for coming along on this not-so-quick rappel down into the dirty depths with me even though we've lost a few readers along the way. *Takes ball cap off and offers a moment of silence for them.* Ah, well… I knew from the start this type of story wasn’t for everyone. *Puts hat back on.* Still, we've managed to pick up a few others: the breathless Bitty, Akibabes25, and NoSarcasmForYou, all bravely stepped into the void which is much appreciated._

_Now let’s get back to our story._

* * *

_So, where did I leave us? Oh, yeah. Readers screaming for vengeance, calling for Derek and John and all the others to pay, and Stiles standing between Derek’s splayed, bound thighs, teasing his ex with his magically enhanced cock and the words..._

“You could have had this…”

And from the expression on his gagged face it’s terribly clear in that instant just how much Derek wants it.

_Wants it..._

_So._

_Fucking._

_Bad._

He needs it like nobody’s business. Every cell in his body is crying for that dick. His dark, sweaty head is lifted, neck muscles straining as he desperately tries to catch a glimpse of it.

Derek is leaking more drool than a Basset hound around the gag in his mouth and his bound cock is no different. He’s craving Stiles’ cock that badly, red-rimmed and watery, his green eyes, silently beg. They’re so round in their want and so damn sorrowful he looks like one of those big-eyed kid paintings.

Stiles ignores him, he’s on a mission. Besides, he knows if he shows any signs of weakening Buffy will kick his ass. So, instead of looking at Derek, he hooks one skinny middle finger through the loop of Derek’s dick piercing and wiggles it.

Derek’s cock is swollen, purpled with blood and desire, and Stiles knows it has to hurt like fuck when he tugs it. The way Derek throws his head back, keening and choking around the gag just confirms it.

That doesn’t stop him though. He uses the ring in Derek’s dick to pull the slut forward onto his newly monstrous cock. As he does, he knows he could have teased Derek more, _should have_ , the prick’s earned it after all, but they’re on the clock and all of a sudden, after waiting two years for this moment, Stiles just wants to get done with this and get on with his life.

The bane in Buffy’s cum lube keeps Derek’s hole from tightening as quickly as it would normally and Stiles should be disappointed that he slips his tip in so easily. It’s nothing like the tightness he’s relived so many times in his memory but the tug of true mate is still there and the silky heat of Derek’s ass feels like heaven around the head of his cock.

“You could have had this…” he whispers again. He almost says Derek’s name, but stops himself because saying it would make this feel too intimate and the opportunity for intimacy ran out a long time ago.

”However you wanted it… I would have given it to you.”

Stiles glances up then and catches his current loves watching him anxiously from the sides. He gives them a strained smile meant to reassure and says louder, “But you fucked that up.

"Thankfully, I’ve found a couple of someones who think I’m worth their honesty.”

It’s hard to say and it hurts, but seeing the love in Buffy and Xander’s eyes goes a long way as a balm. But what’s even more healing is Stiles realizes he mean it. And with that, whatever little bit of bond might have been left in him breaks.

At the same moment, with a thrust of his hips, his cock slides in to its hilt. The second he fully breaches that hot, messy, man cunt, Derek’s whole body stiffens and the sound that slips muffled around the gag is one of agony and ecstasy combined.

But while Derek’s gone rigid, Stiles, despite Deaton’s elixir, starts to soften as the last of their mate bond slips from him. Derek doesn’t know what’s happening but he feels the hot rod in his ass melting and it throws him into a panic.

The gnawing hunger in his hole was about to be sated at last, he knows this somehow, and the knowledge he just might not get this fuck makes him frantic.

In an instant, he’s pumping his hips, contracting his ass pussy around Stiles’ wilting stem. The air fills with desperate whines and cock-muffled pleas as he tries every trick his acrobatic ass knows to keep Stiles with him.

“Stiles?”

It’s Buffy. She knows something’s shifted too, but she’s not sure what.

Still sheathed in Derek’s slutty ass, ignoring the writhing bitch beneath him Stiles exhales a long breath and whispers, “Kiss me?”

Buffy’s eyes widen at the question in the words, then she smiles and steps up.Takes her lover’s jaw in her hand and gives Stiles just exactly what he needs, slow and deep and tender.

At the same time, Xander slips behind Stiles again and embraces him from behind. Soft cock pressed to the crack of Stiles’ ass, long fingers tease Stiles’ nipples as Xander occupies himself with kissing his lover’s neck until Buffy finally feels like sharing.

“You going to fuck him for us, Daddy?” Xander whispers into Stiles’ mouth. “Cause we want to watch you wreck this bitch.”

Between these words and the tender, dirty kisses the blood moves back into Stiles’ cock and his hips begin to pulse. The little thrusts immediately drive Derek crazy. What makes Derek even more unhinged though, is knowing that it’s not him making Stiles hard at all, but the two strangers attending to him.

“Yeah, show us, Babe.” Buffy kisses three different moles on Stiles’ flushed cheek. “Own that ass. Let that cheating dick know just what the fuck he’s missed out on.”

And with the support of his lovers, Stiles starts fucking Derek in earnest and does just that…

* * *

By the time Stiles is finally ready to cum Derek’s eyes are all but permanently rolled back in his head from bliss. His muscled body shines with sweat, and drool, and his own dick’s drippings.

Readying to shoot his load, Stiles slows down long enough to undo the bindings on Derek’s cock and balls. The moment he does, within another two thrusts, Derek’s cock loses it. It convulses like it’s having an epileptic fit spurting jizz everywhere. The strength of the orgasm shoots spunk high enough to paint Derek’s tear-stained face.

Meanwhile his ass is doing its own “happy dance,” muscles spasming around the dick it was born for. The way it wraps around it’s true mate’s thick cock and squeezes makes Stiles shudder and shout as he comes.

Now, you have to remember the first time Stiles shot his load into Derek’s needy hole, it had already been filled by half a dozen lawmen. So, the strength of Stiles’ seed was diluted. Even so, Derek’s body got enough of a taste to know what it wanted, what it needed, but there clearly wasn’t enough of it to fully cement the wolf’s bond.

This time, however, cleaned out and “rested” for the night’s festivities and raw from the ginger, Derek’s cells get the pure hit of “mate.” _Immediately_. And for a moment, just a moment, the relentless ache, the drive for dick, Derek’s ferocious cum hunger, all of these evaporate.

In the space left by their pause realization hits Derek like a ton of bricks. His eyes snap back, their cum-drunk expression replaced by something horribly focused. Meeting the wide-eyed green gaze staring at him with terrible knowing, Stiles gives the inside of one of Derek’s bound thighs a pat.

“Yeah,” he sighs heavily. “You could have had this…” And he starts pulling out of Derek so that only the head of his cock is caught in his ex’s puffy pucker when he adds, “True Mate…”

At this, Derek’s ass gasps around Stiles’ dickhead; then it cinches down tight, as though it can hold him in. It’s no use though, Stiles just gives a little tug, hissing from sex-sensitivity, but in truth, that’s about all he feels when his cock pops all the way out.

_Well, that and a strange, wonderful kind of relief._

Derek on the other hand goes bonkers. He’s weeping so hard he just might drown behind the gag he’s wearing. The dreaded itch in his ass starts to tingle again already but it’s nothing compared to the empty ache in his chest.

He’s full on howling now around the silicone cock in his mouth, trying to break his runed bonds so he can grab Stiles and hold him, keep his true mate with him. _In him_. He stills for only a moment when Stiles shakes his head and says with more firmness than Derek has ever heard from his former twink lover, “No, man. It’s over.”

_And if there was any question, right on cue, there’s a rap on the door to confirm this._

“Hey Kid, five-minute mark,” John shouts from the hallway.

With that, there’s a sudden scramble, Stiles and Buffy righting themselves just enough before they crawl back out the window, the duffle follows. And after a couple minutes of heated conversation, there’s a shift in plans and rather than stay and walk out the front door, Xander joins them.

This means when John returns the room all he finds is an open window and his star, silent, except for Derek’s significant sniffling. This concerns the sheriff a bit, but not overly. _Since Derek tends to cry a lot when he’s fucked and most often because he loves it so much._

A quick sweep of pale eyes over the room shows everything, including his bitch, still appears in its proper place. Stepping over to the camera he sees the footage is there, the machine still recording, John breathes a sigh of relief and wonders why the fuck the kid bolted.

Turning his attention fully to his star at last, he looks over Derek’s body and outside the obvious emotional display, he doesn’t see anything truly amiss.

_I mean, no more than usual._

“Little prick chicken out?” he asks, semi-ignoring the fact Derek is clearly gagged. “I thought that kid looked like a punk.”

But when he moves around to check out his slut’s hole, Derek’s ass tells another tale. His whore’s cunt is wrecked, gaping way more than usual, spasming still and leaking a fuckload of cum and lube.

John pulls a travel pack of wet wipes out of a pocket and wipes Derek’s runny ass. “Man, I can’t wait to see that footage. There was more moxie there than meets the eye, I guess, huh? Bet you fucking loved it. No wonder you’re crying. Must be tears of joy, eh, Champ?”

Then he moves up to Derek’s head. He loosens the gag. He stops for a moment once Derek ‘s face is free to brush a finger down his bitch’s wet, splotchy-red cheek.

“You okay, Hun?” It’s a rare endearment as he wipes Derek’s face, but the look in his bitch’s eyes tells him Derek isn’t snotty from tears of happiness. Something big clearly happened in his absence.

Derek looks away from his pimp/alpha/keeper/lover and whispers, his throat ruined by cock, “Stiles…” Then he shudders and a hoarse sob escapes him.

John just shakes his head and sighs. “We don’t have time for this tonight, Derek. I’ve got the first busload pulling up to the drive now.”

Then he leans down and kisses Derek deeply because that sometimes helps to settle his slut. “You going to pull yourself together for me? Cause we’ve got a contract for twenty films riding on this going well tonight and I can’t have you breaking down again now.”

There’s something simultaneously soothing and inciting in that kiss from the sheriff, his pseudo alpha’s saliva mixing with the trace of “true mate” Derek licks from his slick upper lip. His bottom mouth twitches at that contact; the hunger for a brief moment abates and a moment of clarity pierces through the mate-haze.

Even with this lucidity though, words won’t come to him. _Not that this would change anything, the show must go on, after all._ And despite the fact what just happened with Stiles shattered him in an entirely new way Derek nods, though he knows there’s no possibility he can pull himself together.   

As soon as he nods it’s clear John wasn’t really expecting any other answer, since he gives a crisp whistle and some of his former deputy/ film crew/ costars slip in.

“Wait ‘till you see the cocks I lined up for you, Derek. You’re going to love them!” The Sheriff runs his fingers through Derek’s soaked bangs, made oddly anxious by his slut’s silence. The film staff makes quick work of getting Derek ready even as the Sheriff talks. Efficient swipes of rough cloths clear away the cooling spend on his skin his keeper missed.

“I chose them all special for you. There’s not a one under eight inches, and the thickest is the size of a beer can.” John proudly tells his bound slut; a finger tracing swollen lips.  Then he pulls his bitch’s mouth open and spits into it for good measure in a perverted “good luck” kiss. He watches as Derek dutifully swallows, for a moment losing himself in the fantasy of sending the guys away and burying his thickening cock down that marvelous throat or that wonderfully wrecked ass.

But instead, John orders the guys to just pick Derek up, bound as he is, and move him to the table outside. They’re behind schedule and he wants to get started filming as soon as the first batch of guys hit the ground, because the live pay-per-view feed he sold to about 50,000 internet viewers is scheduled to open in five minutes.

Systems still reeling in shock and strangely buzzing from the sheriff’s kiss, Derek just allows himself to be manhandled by the crew. _After all, there’s nothing like losing oneself in a really good fuck. And Derek knows this better than anyone since he’s been doing it for years._

Carried outside, he’s strapped down on his back, ass tight to the edge of the picnic table on the porch to wait for his hundred studs. The restraints aren’t as tight as before, he can feel some give to the ones binding his arms to the hardwood surface.  Derek tentatively opens his drawn knees wider apart testing his leeway. And while everything else is business as usual around him, he waits, the ache in his heart and the itch in his ass growing stronger with each passing minute.

Meanwhile John has his lead ex-deputy, Jesse, run through a quick equipment check while he goes to greet their great herd of exceptional cocks. However, the welcoming smile he plasters on his face falls the moment he sees the first guy step off the charter bus he’d arranged to ship the studs from the Holiday Inn where most all of them were staying.

“What the holy fuck?”

* * *

While John is cursing, a couple blocks away, Stiles and his lovers are parked in their rental car, curled up in the back seat in a tangle of limbs.

“We don’t have to stay, you know…” Xander brushes his fingers through the short hair at Stiles’ nape while his boyfriend boots up his laptop.

“Yeah… I know...” Stiles has never been very good at multitasking but it only takes him a minute to break into one of the neighborhood’s wireless servers, then he turns his attention to Xander.

“I mean, I’m good. I’m more than good. But I started this and I want to see this thing through to the end.”

On Stiles’ other side Buffy leans over to nip his earlobe, then pulls back with a grin. “I love a man with a plan and the balls to see it through.”

Stiles blushes adorably and rubs his tingling ear. He’s just about to pull up the live feed for Derek’s gangbang when Buffy sets her hand over his flying fingers. He frowns in confusion, his brow dips even deeper when Xander’s hand joins them.

“We love you, you know.”

Hearing these words said in perfect unison Stiles’ heart hasn’t felt so full for a long time.

“I know. I love you guys too.”

There’s a meeting of mouths after he says this, a wet, sweet, sloppy exchange of kisses, and then the three of them settle in to watch the show.

* * *

_And what a show it’s bound to be since fucking Derek was just the first part of their plan. Yeah, see, it isn’t enough to just leave Derek wanting and weeping. Not according to some of you readers anyway. (Jluis and TheFujoshi, to name just a few.)_

_No, I guess for others, in a cheating fic they really want to see the cuckold-er suffer. So, per your request, now Cheating Derek’s true pain is really going to begin._

Because from his research Stiles knows once the true mate bond was rekindled and then once he verbally rejected Derek, the were-slut would quickly become even more insatiable than before: every cell in his wolf’s body screaming for its mate, and given the animalistic nature of Derek’s pussy, it more than anything.

This would lead to Derek giving the performance of his life as he tried to stifle its need on all the fine cocks his police pimp had lined up for him. He’d fuck the shit out of all of them, seeking to quench the fire Stiles had undoubtedly lit in his ass.

But as far as Stiles and his lovers were concerned, Derek didn’t deserve that kind of bounty for his burn. Nor did they want the Sheriff making a mint filming what would be the most sexually charged adult film in history.

So instead, while it made him kind of sick, Stiles had looked up the fat hacker from that fateful prom night. _The guy’s name was_ _Frederick J. Dukes, though he most often went by the user name “TheBlob.”_

Given his size, the guy wasn’t really all that hard to find. And once Stiles laid out his proposal, Fred refused the substantial sum he’d been offered to do this particular “dirty work.” _No, he didn’t want to be paid in money._  What he took in exchange for his work was the promise of being the first in Derek’s lineup of “post-Stiles” fucks.

Stiles was revolted at the proposition but that revulsion only made him more eager. As soon as the contract was written and signed, TheBlob went to work and what he did was cyber magic. _Reaching out around the web he replaced all John’s well… uh… john’s for Derek with a different kind of man, per Stiles instructions._

Not all the guys that met Stiles’ criteria had the money to bid on fucking Derek, so he paid the sale price for everyone. And his recruits certainly didn’t meet John’s physical specifications for “winning bidders.”  To get around this, Fred oversaw and rerouted all the correspondence, and provided fake profiles for all the sheriff’s “hot, big-cocked guys."

Yeah, so after manipulating the applications and the auction for “Bad Dog’s 100 Man Fuckathon,” Fred’s the first guy to waddle off the bus. And the first one of Derek’s fuckers John sees.

_If Stiles had ever been worried about his old man’s ticker before, well, this would have been the moment for it._

Of course, immediately recognized, TheBlob just stands there, all smirking 400 hundred pounds of him, while John rants, and raves, and threatens. Then, just as the sheriff is about to call some of his crew to forcibly roll Fred off the premise, TheBlob holds up his cell phone and shows John his acceptance code.

“The fee I paid will be traced to my bank account. Our deal was sealed, just like everyone else here. So you, gonna tell me you’re going to break our contract? Deny me the ass I paid for?”

The words are said cooly and John shuts up fast. But not just because of what Fred’s just spelled out to him. No, the reason the Sheriff suddenly loses his words is because he looks up and really sees for the first time the “everyone else” the hacker is talking about.

None of these guys, and I mean, None. Of. Them. Even comes remotely close to the studs he thought he’d slotted for his slut. Milling around the yard, being shepherded by stunned looking “Bad Dog” staff into numerical lines based on their acceptance codes, is about the most motley crew the Sheriff’s ever had the sad privilege to witness.

Their body types range in extremes from skeletal twinks to TheBlob’s body doubles. There’s balding middle-aged guys with comb-overs, acne ridden barely-legals, and a few geriatrics being offloaded by mechanical bus ramps while they sit on their scooters. The Sheriff’s also convinced there’s more than a couple homeless guys shipped out from the strip among the crowd.

“This can’t be happening…” John’s horrified whisper is all but lost among the murmured hubbub of the excited ‘studs’.  The second bus pulls up behind the first and he watches unblinkingly as dozens more misfits pile off.

“Oh, but it is, Sheriff!” and the voice Frederick Duke, aka TheBlob, says this in could have won him a super-villain role in any Hollywood Studio. “And if you try and deny all these paying customers, I guarantee you’re going to have a riot on your hands.

“Not to mention your 50,000 Internet subscribers.”

With this, TheBlob turns and lifts one of his huge, meaty arms, “I’m first! Number one here!” he shouts waving his phone. A very pale and perplexed former deputy, Kyle, sees Fred and shoots John a WTF look.

But what Fred’s said is true, failing to deliver here will ruin him in so many ways, so John just shakes his head and yells “Get him to the front of the line, Kyle!” before walking away, rubbing his temples. Hoping to God that as bad as they look, these guys at least have decent dicks.

* * *

While all this chaos is going on around him, Derek drifts. Or at least tries too. His chest feels like it’s been struck with a two ton, steel beam, and his ass feels like it needs the same shoved in it.

He blinks when the sheriff leans down over him, face more worried than he’s ever seen it, and tells him there’s been a little mix up and he’s trying to fix it. In the meantime, John all but begs him to be a good slut for him. "To just lie back and take whatever comes," until he can find a way to end it.

Derek grunts, confused, as his keeper slides a fresh ring gag in his mouth and once it’s buckled, presses a chaste kiss to his forehead. John disappears from view then. Derek lifts his head, straining to find him, but his frantic turning stops and his eyes pop wide when he sees and smells an old, familiar fuck.

“I see you haven’t forgotten me, Bitch.” Fred chuckles as he waddles in between Derek’s splayed thighs, pushing them open wider to accommodate his bulk to the point that Derek whines in discomfort. "Fuck, I can't wait to get into your ass again."

Even as he’s walking away, John hears the questioning cries from Derek’s gagged mouth. Knowing it's a mistake to do so, he turns around to see Derek's face turned towards him, green eyes wide, arms straining against the bane-infused bonds, tongue wagging in his open mouth.  

The Blob has his hands on both of Derek's knees pushing them as far apart as the bindings and Derek’s own body will allow. He shoves himself forward. Sickened with the scene and with himself, John turns away before he sees anymore firsthand, hurrying to the screens on the side to assess how the feed is looking.

Now when he’d gotten to fuck Derek last time, TheBlob had his gut held up in a special sling so Derek could access his cock and ride him to completion. Not here though. Here, he heaves his weighty gut up and drops it on Derek, driving the breath out of him as he moves up and pokes his cock into Derek’s man cunt. _It’s not a bad cock, thick, though nowhere near as thick as the rest of him and long enough at least that, despite his bulk, he manages to get a good number of inches inside._

Before Derek can regain his breath, Fred starts fucking. From the sidelines John stares at the video screens showing the footage with a mounting sense of dread. They’ve got cameras installed everywhere, but from each angle, all you can see with most of them is just the barest bits of Derek buried under a mountain of jiggling Fred flesh as the hacker fucks furiously into him.

John’s eyes are sadly glued to a back view, showing a huge, flat, pimpled and pumping ass. The only bright spot is that at least Derek doesn’t seem to be suffering too much, if the audio is anything to go by.

At first the sheriff could have sworn that Derek was yelling out his son’s name and, later, his own.  Or at least versions that could be said from a gagged mouth. But now Derek is whining and moaning what sounds like muffled “more” and “please” and “fuck me” around the ring gag. _Though it’s kind of hard to make out amidst the accompanying sounds of squishing, slicking, slapping, and sucking flesh._

“How the hell are we going to edit this clusterfuck later, Chief?”

This comes from Jesse who’s staring from monitor to monitor at the mounds of pulsating, pink flesh. He then nods over to the lines of eager outcasts, some of them with their dicks out, jerking themselves to hardness as they watch Fred fuck with wild, obese abandon.

 _Cause who the hell would_ by _a DVD of this, right?_

_(I would.)_

“Hell if I know. Just keep rolling.” John hates himself as he says this, his usual jealousy at having to share his slut stronger than usual, but they need this.

_Cause after the Fuckathon, the other studio contract is for exclusive films under his complete control. It’s all part of his plan to make a mint and then retire them both._

_And how will he do this with his bitch needing something in his greedy holes every hour of the day?_

_Well, the sheriff’s found a couple reputable witch doctors (Deaton refused to help them after what they did to Stiles) who’ve promised to sell him a cure for Derek’s unbridled lust, one that will not only sate his cock hunger, but bind Derek to him in its absence._

_And it’s not cheap._

The sheriff calls over to his website manager then. “And keep on top of the complaints. No refunds as long as he gets through them all, that’s the rule. Got it! I don’t care what they threaten you with!”

________________________________________

“Oh, God!” Buffy shrieks with disgust, completely unaware of the irony of her exclamation over “fat fucking” as she’s busy stuffing her mouth with some of the snacks from the cooler they’d brought along with them: cold fried chicken and cookie dough.

Xander is staring at her food combination with the same sort of mock horror currently on Buffy's face, while Stiles’ eyes are glued on the screen watching his ex get pounded. _(Yeah, that’s kind of a pun there.)_

He knows the bond is broken, he also knows he’s getting even and this shouldn’t be hot. But it kind of is: seeing someone buff and godlike as Derek, getting his ass thrashed by a guy, _who, let’s admit it,_ is pretty much the complete opposite.

Now, Deaton’s potion hasn’t quite worn off, so it’s easy for Xander to notice right away when his boyfriend starts getting hard. Stiles groans and lifts the laptop up, when Xander unbuckles his pants and slides them off, deciding to indulge in a “snack” of his own while Stiles keeps watching.

And apparently Stiles isn’t the only one who finds Fred fucking Derek holds a certain perverse appeal. _I mean, after the first thousand or so complaints and WTF messages light up Bad Dog’s boards, new subscriptions start trickling in._

The numbers jump a little too when Fred finishes, pulls his sticky dick out, and Derek starts begging from behind the gag for the fat fucker not to leave him, his garbled words much more audible once he’s excavated from under that mountain of flesh.

Fred laughs and promises to come back "for sloppy one hundred and firsts" if he can. Oddly as TheBlob walks away, the volume of Derek's pitiful protests at being left increases.

He doesn’t get to make this noise for long though, as the next three guys in line surge forward.

**Notes for the Chapter:**

> Okay, I have to say this chapter was for Benn_Xavier, too. Cause he deserved a treat. And wait until you see the art he made for this fic. Amazing! You'll get to see it in the next (and last?) chapter.
> 
> Also, any of you recognize Fred? It's another one of my little crossovers.
> 
> Thanks for reading.


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